Oxime derivative and bactericide containing the same as active ingredient

ABSTRACT

A compound represented by general formula (I) or a salt thereof, a process for producing the same, an intermediate for the production thereof, and a bactericide (fungicide) containing the same as the active ingredient wherein R 1  represent optionally substituted aryl, optionally substituted heterocycle, mono- or di-substituted methyleneamino, optionally substituted (substituted imino)methyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, substituted carbonyl or substituted sulfonyl; R 2  represents alkyl, alkenyl, alkynyl or cycloalkyl; R 3  represents optionally substituted heterocycle; R 4  represents hydrogen, alkyl, alkoxy, halogen, nitro, cyano or haloalkyl; M represents oxygen, S(O)i (i being 0, 1 or 2), NR 16  (R 16  being hydrogen, alkyl or acyl) or a single bond; n represents 0 or 1, provided n represent 1 when R3 represents imidazol-1-yl or 1H-1, 2, 4-triazol-1-yl; and the symbol˜represents the E form, Z form or a mixture thereof.

This application is a divisional of application Ser. No. 09/370,255,filed Aug. 9, 1999, which in turn is a divisional of application Ser.No. 08/693,224, filed Aug. 21, 1996, now U.S. Pat. No. 6,048,885, whichis a 371 of PCT/JP95/00604, filed Mar. 30, 1995, claiming the benefit ofpriority of foreign application, JP 087819/1994 filed Apr. 1, 1994.

TECHNICAL FIELD

The present invention relates to an oxime derivative, particularly aheterocyclic compound substituted with α-(o-substitutedoxyimino)-2-substituted benzyl, a process for producing it,intermediates therefor, and a bactericide (fungicide) containing it asan active ingredient.

BACKGROUND ART

Compounds containing α-(o-substituted oxyimino)-benzyl known so farinclude benzohydroxymoylazole derivatives having insecticidal activity(JP-A 1-308260, JP-A 5-1046, WO92/09581, JP-A 5-331011, JP-A 5-331012,JP-A 6-41086), oxime derivatives having insecticidal activity (JP-A3-68559), 1-azolyl-substituted oxime ethers having fungicidal activity(JP-A 60-87269), etc.

The present invention is to provide a compound having more potentfungicidal activity, higher utility, etc., than the known compounds aswell as low toxicity.

DISCLOSURE OF INVENTION

The present inventors have intensively studied to achieve the aboveobject. As a result, it has been found that a heterocyclic compoundsubstituted with α-(-o-substituted oxyimino)-2-substituted benzyl haspotent fungicidal activity. After further studies, the present inventionhas been completed.

The present invention provides:

1. A compound of the formula (I):

 wherein R¹ is optionally substituted aryl, an optionally substitutedheterocyclic group, mono or disubstituted methyleneamino, optionallysubstituted (substituted imino)methyl, optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,substituted carbonyl or substituted sulfonyl; R² is alkyl, alkenyl,alkynyl or cycloalkyl; R³ is an optionally substituted heterocyclicgroup; R⁴ is hydrogen, alkyl, alkoxy, halogen, nitro, cyano orhalogenated alkyl; M is an oxygen atom, S(O)_(i) (in which i is 0, 1 or2), NR¹⁶ (in which R¹⁶ is hydrogen, alkyl or acyl) or a single bond; nis 0 or 1, provided that, when R³ is imidazol-1-yl or1H-1,2,4-triazol-1-yl, n is 1; and˜indicates an E- or Z-isomer or amixture thereof; or a salt thereof;

2. A compound according to the above item 1, wherein the optionallysubstituted heterocyclic group represented by R¹ is pyridyl,pyrimidinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, isoxazolyl,isothiazolyl, thiadiazolyl, pyridazinyl, pyrrolyl, pyrazolyl, furyl,thienyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl,quinolyl, indolyl, benzisothiazolyl, benzisoxazolyl or pyrazinyl, eachof which is unsubstituted or substituted, or a salt thereof;

3. A compound according to the above item 1, wherein R¹ is phenyl or aheterocyclic group, each of which is unsubstituted or substituted with 1or 2 substituents selected from the group consisting of halogen, loweralkyl, halogenated lower alkyl, lower alkoxy, lower alkylthio, phenyl,phenoxy and nitro, or a salt thereof;

4. A compound according to the above item 1, wherein R¹ is phenyl;phenyl substituted with halogen and/or lower alkyl; or pyridylsubstituted with halogen and/or halogenated lower alkyl; or a saltthereof:

5. A compound according to the above item 1, wherein R¹ is phenyl,2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl,3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 2,5-dimethylphenyl,2,6-dimethylphenyl, 4-chloro-2-methylphenyl, 2-chloropyridin-3-yl,3,5-dichloro-pyridin-2-yl, 5-trifluoromethylpyridin-2-yl,5-trifluoromethyl-3-chloropyridin-2-yl or3-trifluoromethyl-5-chloropyridin-2-yl, or a salt thereof;

6. A compound according to the above item 1, wherein R¹ is a group ofthe formula (a):

 wherein R⁹ and R¹⁰ are the same or different and are hydrogen,optionally substituted alkyl, acyl, alkylthio, alkylsulfinylalkylsulfonyl, optionally substituted amino, cycloalkyl, optionallysubstituted aryl or an optionally substituted heterocyclic group, or R⁹and R¹⁰ are linked together to form a monocyclic or polycyclic ringwhich may contain a heteroatom, or a salt thereof;

7. A compound according to the above item 1, wherein R⁹ and R¹⁰ are thesame or different and are hydrogen, alkyl, haloalkyl, alkoxyalkyl,alkylcarbonyl, optionally substituted phenyl, optionally substitutednaphthyl or an optionally substituted heterocyclic group, or R⁹ and R¹⁰are linked together to form a cyclopentane or cyclohexane ring which mayform a condensed ring with another ring, or a salt thereof;

8. A compound according to the above item 1, wherein R⁹ is phenyl whichis unsubstituted or substituted with 1 to 3 substituents selected fromthe group consisting of halogen, optionally substituted alkyl,optionally substituted hydroxyl, alkylthio, optionally substitutedamino, nitro, phenyl and cyano, or a salt thereof;

9. A compound according to the above item 1, wherein R⁹ is phenyl whichis unsubstituted or substituted with 1 to 3 substituents selected fromthe group consisting of chlorine, methyl, trifluoromethyl and methoxy,or a salt thereof;

10. A compound according to the above item 1, wherein R⁹ is morpholino,pyridyl, pyridazinyl, pyrazolyl, pyrimidinyl, furyl, thienyl, oxazolyl,isoxazolyl, benzothiazolyl, quinolyl, quinazolinyl or pyrazinyl, each ofwhich is unsubstituted or substituted, or a salt thereof;

11. A compound according to the above item 1, wherein R¹⁰ is hydrogen oralkyl, or a salt thereof;

12. A compound according to the above item 1, wherein R¹⁰ is hydrogen,methyl or ethyl, or a salt thereof;

13. A compound according to the above item 1, wherein R² is alkyl oralkenyl, or a salt thereof;

14. A compound according to the above item 1, wherein R² is methyl,ethyl or allyl, or a salt thereof;

15. A compound according to the above item 1, wherein R³ is isoxazolyl,oxazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrolyl, pyrazolyl,furyl, thienyl, imidazolyl, triazolyl, tetrazolyl, oxadiazolyl,thiazolinyl, isoxazolinyl, imidazolinyl, oxazolinyl or thiazolidinyl,each of which is unsubstituted or substituted, or a salt thereof;

16. A compound according to the above item 1, wherein R³ is imidazolyl;imidazolyl substituted with lower alkyl; imidazolinyl; triazolyl;imidazolinyl substituted with lower alkyl; isoxazolyl; isoxazolylsubstituted with lower alkyl; oxadiazolyl; oxadiazolyl substituted withlower alkyl; isoxazolinyl; isoxazolinyl substituted with lower alkyl;oxazolinyl; pyrazolyl; pyrazolyl substituted with lower alkyl;thiazolinyl; furyl; tetrazolyl substituted with lower alkyl; oxazolyl;isothiazolyl substituted with lower alkyl; thiazolidinyl; orthiazolidinyl substituted with lower alkyl; or a salt thereof;

17. A compound according to the above item 1, wherein R³ isimidazol-1-yl, imidazol-2-yl, 1-methylimidazol-2-yl,2-methylimidazol-1-yl, 4-methylimidazol-1-yl, 5-methylimidazol-1-yl,2-imidazolin-2-yl, 1H-1,2,4-triazol-1-yl, 1-methyl-2-imidazolin-2-yl,isoxazol-3-yl, 3-methylisoxazol-5-yl, 5-methylisoxazol-3-yl,5-methyl-1,2,4-oxadiazol-3-yl, 3-ethyl-1,2,4-oxadiazol-5-yl,2-isoxazolin-3-yl, 2-oxazolin-2-yl, 3-methyl-2-isoxazolin-5-yl,pyrazol-1-yl, 1-methylpyrazol-5-yl, 2-thiazolin-2-yl, 2-furyl,3-methylisothiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,1,3,4-oxadiazol-2-yl, 5-methyl-1,3,4-oxadiazol-2-yl,2-methyltetrazol-5-yl, oxazol-5-yl, isoxazol-5-yl, thiazolidin-2-yl or3-methylthiazolidin-2-yl, or a salt thereof;

18. A compound according to the above item 1, wherein R⁴ is hydrogen, ora salt thereof;

19. A compound according to the above item 1, wherein M is an oxygenatom, or a salt thereof;

20. A fungicidal composition comprising a compound according to any oneof the above items 1 to 19 or a salt thereof as an active ingredient;

21. A process for producing a compound of the formula (I):

 wherein each symbol is as defined in the above item 1, which comprisesreacting the compound of the formula (V):

 wherein A is halogen and the other symbols are as defined in the aboveitem 1, with a compound of the formula (X):

R³—H  (X)

 wherein R³ is an optionally substituted heterocyclic group;

22. A process according to the above item 21, wherein R³ is pyrrolyl,imidazolyl, pyrazolyl or triazolyl, each of which is unsubstituted orsubstituted;

23. A compound of the formula (V):

 wherein A is halogen and the other symbols are as defined in the aboveitem 1, or a salt thereof;

24. A compound according to the above item 23, wherein M is an oxygenatom, or a salt thereof;

25. A compound of the formula (XIV):

 wherein each symbol is as defined in the above item 1, provided that,when M is an oxygen atom and R³ is isoxazol-4-yl, n is 1, or a saltthereof;

26. A compound according to the above item 25, wherein M is an oxygenatom, or a salt thereof; and,

27. A compound of the formula (XLVIII):

 wherein P is a protective group of a hydroxyl group, and the othersymbols are as defined in the above item 1, or a salt thereof.

The term “lowers” used herein means having 1 to 8 carbon atoms,preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms,unless otherwise indicated.

The aryl of the optionally substituted aryl represented by R¹ includesaryl having 6 to 14 carbon atoms such as phenyl, naphthyl, etc.

The optionally substituted heterocyclic group represented by R¹ includesunsubstituted or substituted heterocyclic groups. Examples of theheterocyclic group include 5- to 7-membered heterocyclic groupscontaining 1 to 4 heteroatoms selected from nitrogen, sulfur and oxygenin the ring, such as pyridyl (e.g., pyridin-2-yl, pyridin-3-yl),pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl), benzoxazolyl (e.g.,benzoxazol-2-yl), benzothiazolyl (e.g., benzothiazol-2-yl),benzimidazolyl, isoxazolyl (e.g., isoxazol-3-yl, isoxazol-5-yl),isothiazolyl, thiadiazolyl [e.g., 1,3,4-thiadiazolyl (e.g.,1,3,4-thiadiazol-2-yl), 1,2,4-thiadiazolyl, etc.], pyridazinyl,pyrrolyl, pyrazolyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl,oxadiazolyl (e.g., 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, etc.),triazolyl (e.g., 1,2,3-triazolyl, 1,2,4-triazolyl, etc.), quinolyl(e.g., quinolin-2-yl), indolyl, benzisothiazolyl, benzisoxazolyl,pyrazinyl (e.g., pyrazin-2-yl), etc. The heterocyclic group may form acondensed cyclic group with a carbocycle or another heterocycle. Theheterocycle has a bond to M at any possible position in the ring.

The substituent of the substituted aryl and substituted heterocyclicgroup represented by R¹ includes, for example, lower alkyl (e.g.,methyl, ethyl, propyl, butyl, etc.), lower alkenyl (e.g., vinyl, allyl,crotyl, etc.), lower alkynyl (e.g., ethynyl, propargyl, butynyl, etc.),cycloalkyl (e.g., cyclopropyl, cyclopentyl, cyclohexyl, etc.),cycloalkenyl (e.g., cyclopentenyl, cyclohexenyl, etc.), lower alkanoyl(e.g., acetyl, propionyl, isobutyryl, etc.), lower alkylsilyl (e.g.,methylsilyl, ethylsilyl, propylsilyl, butylsilyl, etc.), halogenatedlower alkyl (e.g., trifluoromethyl, trichloromethyl, chloromethyl,2-bromoethyl, 1,2-dichloropropyl, etc.), di(lower)alkylamino (e.g.,dimethylamino, diethylamino, etc.), phenyl, phenyl(lower)alkyl (e.g.,benzyl, phenethyl, etc.), phenyl(lower)alkenyl (e.g., styryl, cinnamyl,etc.), furyl(lower)alkyl (e.g., 3-furylmethyl, 2-furylethyl, etc.),furyl(lower)alkenyl (e.g., 3-furylvinyl, 2-furylallyl, etc.), halogen(e.g., fluorine, chlorine, bromine, iodine), nitro, cyano, loweralkylthio (e.g., methylthio, ethylthio, propylthio, etc.), —OR¹¹[wherein R¹¹ is hydrogen, lower alkyl group (e.g., methyl, ethyl,propyl, etc.), lower alkenyl (e.g., vinyl, allyl, crotyl, etc.), loweralkynyl (e.g., ethynyl, 2-propynyl, 3-butynyl, etc.), lower alkanoyl(e.g., acetyl, propionyl, butyryl, etc.), phenyl, lower alkoxyphenyl(e.g., 3-methoxyphenyl, 4-ethoxyphenyl, etc.), nitrophenyl (e.g.,3-nitrophenyl, 4-nitrophenyl, etc.), phenyl(lower)alkyl (e.g., benzyl,phenethyl, phenylpropyl, etc.), cyanophenyl(lower)alkyl (e.g.,3-cyanophenylmethyl, 4-cyanophenylethyl, etc.), benzoyl,tetrahydropyranyl, pyridyl, trifluoromethylpyridyl, pyrimidinyl,benzothiazolyl, quinolyl, benzoyl(lower)alkyl (e.g., benzoylmethyl,benzoylethyl, etc.), benzensulfonyl, or lower alkylbenzenesulfonyl(e.g., toluenesulfonyl, etc.)], —CH₂—Z—R¹² [wherein Z is —O—, —S— or—NR¹³—(in which R¹³ is hydrogen or lower alkyl), R¹² is phenyl,halophenyl (e.g., 2-chlorophenyl, 4-fluorophenyl, etc.), loweralkoxyphenyl (e.g., 2-methoxyphenyl, 4-ethoxyphenyl, etc.), pyridyl, orpyrimidinyl], etc. In particular, halogen, lower alkyl, halogenatedlower alkyl, lower alkoxy, lower alkylthio, phenyl, phenoxy and nitroare preferred. More preferred are halogen and lower alkyl. Thesubstituent may be at any possible position in the ring. The number ofthe substituent(s) is 1 to 5, preferably 1 to 4, more preferably 1 to 3.The substituents may be the same or different.

R¹ is preferably phenyl or a heterocyclic group each of which isunsubstituted or substituted with 1 or 2 substituents selected from thegroup consisting of halogen, lower alkyl, halogenated lower alkyl, loweralkoxy, lower alkylthio, phenyl, phenoxy and nitro. Preferred examplesof R¹ include phenyl, phenyl substituted with halogen (preferablychlorine) and/or lower alkyl (preferably methyl) (e.g., 2-chlorophenyl,3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl,4-methylphenyl, 2-ethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl,4-chloro-2-methylphenyl, etc.), pyridyl substituted with halogen(preferably chlorine) and/or halogenated lower alkyl (preferablytrifluoromethyl) (e.g., 2-chloropyridin-3-yl, 3,5-dichloropyridin-2-yl,5-trifluoromethylpyridin-2-yl, 5-trifluoromethyl-3-chloropyridin-2-yl,3-trifluoromethyl-5-chloropyridin-2-yl, etc.), etc.

Mono or disubstituted methyleneamino is also preferred for R¹. The monoor disubstituted methyleneamino is represented, for example, by theabove formula (a). The alkyl of the optionally substituted alkylrepresented by R⁹ or R¹⁰ in the formula (a) includes, for example, alkylhaving 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, such asmethyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl,hexyl, etc. In particular, methyl or ethyl is preferred. Examples of thesubstituted alkyl include haloalkyl containing as the substituent atleast one halogen (e.g., fluorine, chlorine, bromine, iodine, preferablyfluorine) (e.g., difluoromethyl, trifluoromethyl, chloromethyl,2-bromoethyl, 2,3-dichloropropyl, etc.); alkoxyalkyl containing as thesubstituent alkoxy having 1 to 8 carbon atoms, preferably 1 to 4 carbonatoms (e.g., methoxy, ethoxy, propoxy, butoxy, etc.)(e.g.,methoxymethyl, ethoxymethyl, methoxyethyl, etc.); etc. In particular,trifluoromethyl is preferred for the haloalkyl, and methoxymethyl ispreferred for the alkoxyalkyl.

The acyl represented by R⁹ or R¹⁰ includes, for example, alkylcarbonyl,arylcarbonyl, etc. Examples of the alkylcarbonyl includes C₁₋₆alkylcarbonyl, preferably C₁₋₄ alkylcarbonyl, such as acetyl,trifluoroacetyl, propionyl, butyryl, etc. Examples of the arylcarbonylinclude C₆₋₁₄ arylcarbonyl such as benzoyl, naphthoyl, etc.

The alkyl of the alkylthio, alkylsulfinyl and alkylsulfonyl representedby R⁹ or R¹⁰ includes the above alkyl of the optionally substitutedalkyl represented by R⁹ or R¹⁰.

The optionally substituted amino represented by R⁹ R¹⁰ includes, forexample, amino, amino mono or disubstituted with alkyl having 1 to 8carbon atoms, preferably 1 to 4 carbon atoms (e.g., monomethylamino,dimethylamino, monoethylamino, etc.), amino monosubstituted with formyl,amino monosubstituted with alkylcarbonyl having 2 to 8 carbon atoms,preferably 2 to 4 carbon atoms (e.g., methylcarbonyl-amino, etc.), etc.

The cylcloalkyl represented by R⁹ or R¹⁰ includes cycloaklyl having 3 to7 carbon atoms, preferably 5 to 6 carbon atoms, such as cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.

The optionally substituted aryl represented by R⁹ or R¹⁰ includes, forexample, C₆₋₁₄ aryl such as phenyl, naphthyl (e.g., 1-naphthyl, etc.),fluorenyl, etc. In particular, phenyl is preferred. The aryl may besubstituted at any possible position in the group. The number of thesubstituent(s) is 1 to 3. Examples the substituent include halogen,optionally substituted alkyl, optionally substituted hydroxyl,alkylthio, optionally substituted amino, nitro, phenyl, cyano, etc.

Examples of the halogen as the substituent of the optionally substitutedaryl represented by R⁹ or R¹⁰ include fluorine, chlorine, bromine, andiodine.

Examples of the optionally substituted alkyl as the substituent of theoptionally substituted aryl represented by R⁹ or R¹⁰ include theoptionally substituted alkyl represented by R¹ described hereinafter. Ofthem, alkyl or haloalkyl, in particular methyl or trifluoromethyl, ispreferred.

Examples of the optionally substituted hydroxyl as the substituent ofthe optionally substituted aryl represented by R⁹ or R¹⁰ includehydroxyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, aryloxy, etc. Thealkoxy includes, for example, alkoxy having 1 to 8 carbon atoms,preferably 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy,butoxy, etc. In particular, methoxy is preferred. The alkenyloxyincludes, for example, alkenyloxy having 2 to 8 carbon atoms, preferably2 to 4 carbon atoms, such as vinyloxy, allyloxy, crotyloxy, etc. Inparticular, allyloxy is preferred. The alkynyloxy includes, for example,alkynyloxy having 2 to 8 carbon atoms, preferably 2 to 4 carbon atoms,such as ethynyloxy, propargyloxy, butynyloxy, etc. In particular,propargyloxy is preferred. The haloalkoxy includes alkoxy describedabove which is substituted with at least one halogen (e.g., fluorine,chlorine, bromine iodine) such as difluoromethoxy, trifluoromethoxy,chloromethoxy, etc. In particular, difluoromethoxy is preferred. Thearyloxy includes, aryloxy having 6 to 12 carbon atoms, preferably 6 to 8carbon atoms, such as phenoxy, naphthoxy, etc.

Examples of the alkylthio as the substituent of the optionallysubstituted aryl represented by R⁹ or R¹⁰ include alkylthio having 1 to8 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 2carbon atoms, such as methylthio, ethylthio, propylthio, butylthio, etc.In particular, methylthio is preferred.

Examples of the optionally substituted amino as the substituent of theoptionally substituted aryl represented by R⁹ or R¹⁰ include amino,amino mono or disubstituted with alkyl having 1 to 8 carbon atoms,preferably 1 to 4 carbon atoms (e.g., monomethylamino, dimethylamino,monoethylamino, etc.), etc.

The optionally substituted heterocyclic group represented by R⁹ or R¹⁰includes, for example, heterocyclic groups containing 1 to 4, preferably1 to 2 heteroatoms (e.g., oxygen, nitrogen, sulfur, etc.) in the ring.At any possible position in the ring, the heterocyclic group containsthe bond to the methylene carbon atom in the formula (a). Examples ofthe heterocyclic group include morpholinyl, pyridyl, pyridazinyl,pyrazolyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl,benzothiazolyl, quinolyl, quinazolinyl, pyrazinyl, etc. In particular,morpholinyl (e.g., morpholino, etc.), furyl (e.g., 2-furyl, etc.),thienyl (e.g., 2-thienyl, etc.), pyridyl (e.g., 2-pyridyl, etc.),pyrazinyl (e.g., 2-pyrazinyl, etc.), or pyrimidinyl (e.g.,2-pyrimidinyl, etc.) is preferred. The heterocyclic group isunsubstituted or substituted. Examples of the substituent include theabove substituents of the optionally substituted aryl represented by R⁹or R¹⁰.

The monocyclic or polycyclic ring which may contain a heteroatom and isformed by R⁹ and R¹⁰ is a 4 to 8 membered ring which is formed by R⁹ andR¹⁰ together with the carbon atom to which R⁹ and R¹⁰ are attached andwhich may contain at least one heteroatom (e.g., oxygen, nitrogen,sulfur, etc.). The ring may form a condensed ring with another ring.Examples of the monocyclic or polycyclic ring include cyclopentane,cyclohexane, indan, 1,2,3,4-tetrahydro-naphthalene,5,6,7,8-tetrahydroquinoline, 4,5,6,7-tetrahydrobenzo[b]furan, etc. Atany possible position in the ring, the monocyclic or polycyclic ringcontains the bivalent bond to the methyleneamino nitrogen atom.

R⁹ is preferably phenyl unsubstituted or substituted with 1 to 3substituents selected from the group consisting of halogen (preferablychlorine), optionally substituted alkyl [e.g., alkyl (preferably inparticular methyl), haloalkyl (preferably trifluoromethyl), alkoxyalkyl,etc.], optionally substituted hydroxyl [e.g., hydroxyl, alkoxy(preferably methoxy), alkenyloxy, alkynyloxy, haloalkoxy, aryloxy,etc.], alkylthio, optionally substituted amino, nitro, phenyl and cyano;or morpholino, pyridyl, pyridazinyl, pyrazolyl, pyrimidinyl, furyl,thienyl, oxazolyl, isoxazolyl, benzothiazolyl, quinolyl, quinazolinyl orpyrazinyl, each of which is unsubstituted or substituted.

R¹⁰ is preferably hydrogen or alkyl (preferably methyl or ethyl).

The optionally substituted (substituted imino)methyl represented by R¹is represented, for example, by the formula (b):

wherein R¹⁴ and R¹⁵ have the same meanings as the above R¹⁰ and R⁹,respectively.

The optionally substituted alkyl represented by R¹ includes, forexample, alkyl having 1 to 8 carbon atoms, preferably 1 to 4 carbonatoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl,t-butyl, pentyl, hexyl, etc. In particular, methyl and ethyl arepreferred. The substituted alkyl includes, for example, haloalkylcontaining as the substituent at least one halogen atom (e.g., fluorine,chlorine, bromine, iodine, preferably fluorine)(e.g., difluoromethyl,trifluoromethyl, chloromethyl, 2-bromoethyl, 2,3-dichloropropyl, etc.);alkoxyalkyl groups containing as the substituent alkoxy having 1 to 8carbon atoms, preferably 1 to 4 carbon atoms (e.g., methoxy, ethoxy,propoxy, butoxy, etc.)(e.g., methoxymethyl ethoxymethyl, methoxyethyl,etc.), etc. In particular, trifluoromethyl is preferred for thehaloalkyl, and methoxymethyl is preferred for the alkoxyalkyl.

The optionally substituted alkenyl represented by R¹ includes, forexample, alkenyl having 2 to 8 carbon atoms, preferably 3 to 6 carbonatoms, such as allyl, propenyl, isopropenyl, butenyl, isobutenyl,pentenyl, hexenyl, hexadienyl, etc. In particular, allyl is preferred.When the alkenyl is substituted, the substituent is, for example,halogen (e.g., fluorine, chlorine, bromine, iodine, preferablyfluorine), alkoxy having 1 to 8, preferably 1 to 4 carbon atoms (e.g.,methoxy, ethoxy, propoxy, butoxy, etc.), etc.

The alkynyl represented by R¹ includes, for example, alkynyl having 2 to6 carbon atoms, preferably 2 to 4 carbon atoms, such as propargyl,ethynyl, butynyl, etc. When the alkynyl is substituted, the substituentis, for example, halogen (e.g., fluorine, chlorine, bromine, iodine,preferably fluorine), alkoxy having 1 to 8 carbon atoms, preferably 1 to4 carbon atoms (e.g., methoxy, ethoxy, propoxy, butoxy, etc.), etc.

The substituted carbonyl represented by R¹ includes, for example,(optionally substituted alkyl)carbonyl, (optionally substitutedaryl)carbonyl, (optionally substituted heterocyclic group)carbonyl, etc.

The substituted sulfonyl represented by R¹ includes, for example,(optionally substituted alkyl)sulfonyl, (optionally substitutedaryl)sulfonyl, (optionally substituted heterocyclic group)sulfonyl, etc.

The optionally substituted alkyl, optionally substituted aryl andoptionally substituted heterocyclic group in the substituted carbonyl orsubstituted sulfonyl include those represented by R¹ described above.

The alkyl represented by R² includes, for example, alkyl having 1 to 6carbon atoms, preferably 1 to 4 carbon atoms, such as methyl, ethylpropyl, isopropyl, butyl, isobutyl, t-butyl, etc. In particular, methylor ethyl is preferred.

The alkenyl represented by R² includes, for example, alkenyl having 2 to8 carbon atoms, preferably 3 to 6 carbon atoms, such as allyl, propenyl,isopropenyl, butenyl, isobutenyl, pentenyl, hexenyl, hexadienyl, etc. Inparticular, allyl is preferred.

The alkynyl represented by R² includes, for example, alkynyl having 2 to6 carbon atoms, preferably 2 to 4 carbon atoms, such as propargyl,ethynyl, butynyl, etc.

The cycloalkyl represented by R² includes, for example, cycloalkylhaving 3 to 8 carbon atoms, preferably 3 to 6 carbon atoms, such ascyclopropyl, cyclopentyl cyclohexyl, etc.

R² is preferably alkyl or alkenyl. In particular, methyl, ethyl andallyl are preferred.

The optionally substituted heterocyclic group represented by R³ includesunsubstituted or substituted heterocyclic groups. The heterocyclic groupis a 5 to 7 membered heterocyclic group containing in the ring 1 to 4heteroatoms selected from nitrogen, sulfur and oxygen. Examples of theheterocyclic group include isoxazolyl (e.g., isoxazol-3-yl,isoxazol-5-yl), oxazolyl (e.g., oxazol-2-yl, oxazol-5-yl), thiazolyl(e.g., thiazol-2-yl), isothiazolyl (e.g., isothiazol-5-yl), thiadiazolyl[e.g., 1,3,4-thiadiazolyl (e.g., 1,3,4-thiadiazol-2-yl),1,2,4-thiadiazolyl, etc.], pyrrolyl, pyrazolyl (e.g., pyrazol-1-yl,pyrazol-5-yl), furyl (e.g., 2-furyl), thienyl (e.g., 2-thienyl),imidazolyl (e.g., imidazol-1-yl, imidazol-2-yl), triazolyl [e.g.,1,2,4-triazolyl (e.g., 1H-1,2,4-triazol-1-yl, 4H-1,2,4-triazol-4-yl,1,2,4-triazol-5-yl), etc.], tetrazolyl (e.g., 1H-tetrazol-5-yl,2H-tetrazol-5-yl), oxadiazolyl [e.g., 1,3,4-oxadiazolyl (e.g.,1,3,4-oxadiazol-2-yl), 1,2,4-oxadiazolyl (e.g., 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl), etc.], thiazolinyl (e.g., 2-thiazolin-2-yl),isoxazolinyl (e.g., 2-isoxazolin-3-yl), imidazolinyl (e.g.,2-imidazolin-2-yl), oxazolinyl (e.g., 2-oxazolin-2-yl), thiazolidinyl,etc. The heterocyclic group may form a condensed ring with a carbocycleor another heterocycle. At any possible position, the heterocyclic groupcontains a bond to the oxime carbon atom in the formula (I).

Examples of the substituent of the substituted heterocyclic grouprepresented by R³ include the above substituents of the substitutedheterocyclic group represented by R¹. In particular, halogenated loweralkyl or lower alkyl is prefered.

R³ is preferably imidazolyl (e.g., imidazol-1-yl, imidazol-2-yl, etc.),imidazolinyl (e.g., 2-imidazolin-2-yl, etc.), triazolyl (e.g.,1H-1,2,4-triazol-1-yl, etc.), isoxazolyl (e.g., isoxazol-3-yl,isoxazol-5-yl, etc.), oxazolyl (e.g., oxazol-2-yl, etc.), tetrazolyl(e.g., 1H-tetrazol-5-yl, etc.), oxadiazolyl (e.g., 1,2,4-oxadiazol-3-yl,1,3,4-oxadiazol-2-yl, etc.), isoxazolinyl (e.g., 2-isoxazolin-3-yl,2-isoxazolin-5-yl, etc.), oxazolinyl (e.g., 2-oxazolin-2-yl, etc.),pyrazolyl (e.g., pyrazol-1-yl, pyrazol-5-yl, etc.), thiazolinyl (e.g.,2-thiazolin-2-yl, etc.), furyl (2-furyl, etc.), isothiazolyl (e.g.,isothiazol-5-yl, etc.), thiazolidinyl (e.g., thiazolidin-2-yl, etc.),etc., each of which is unsubstituted or substituted.

R³ is more preferably imidazolyl (e.g., imidazol-1-yl, imidazol-2-yl,etc.); imidazolyl substituted with lower alkyl (preferably methyl)(e.g., 1-methylimidazol-2-yl, 2-methylimidazol-1-yl,4-methylimidazol-1-yl, 5-methylimidazol-1-yl, etc.); imidazolinyl (e.g.,2-imidazolin-2-yl, etc.); triazolyl (e.g., 1H-1,2,4-triazol-1-yl, etc.);imidazolinyl substituted with lower alkyl (preferably methyl) (e.g.,1-methyl-2-imidazolin-2-yl, etc.); isoxazolyl (e.g., isoxazol-3-yl,isoxazol-5-yl, etc.); isoxazolyl substituted with lower alkyl(preferably methyl) (e.g., 3-methylisoxazol-5-yl, 5-methylisoxazol-3-yl,etc.); oxadiazolyl (e.g., 1,2,4-oxadiazol-3-yl, 1,3,4-oxadiazol-2-yl,etc.); oxadiazolyl substituted with lower alkyl (preferably methyl orethyl) (e.g., 5-methyl-1,2,4-oxadiazol-3-yl,5-methyl-1,3,4-oxadiazol-2-yl, 3-ethyl-1,2,4-oxadiazol-5-yl, etc.);isoxazolinyl (e.g., 2-isoxazolin-3-yl, etc.); isoxazolinyl substitutedwith lower alkyl (preferably methyl) (e.g., 3-methyl-2-isoxazolin-5-yl,etc.); oxazolinyl (e.g., 2-to oxazolin-2-yl, etc.); pyrazolyl (e.g.,pyrazol-1-yl, etc.); pyrazolyl substituted with lower alkyl (preferablymethyl) (e.g., 1-methylpyrazol-5-yl, etc.); thiazolinyl (e.g.,2-thiazolin-2-yl, etc.); furyl (e.g., 2-furyl, etc.); tetrazolylsubstituted with lower alkyl (preferably methyl) (e.g.,2-methyltetrazol-5-yl, etc.); isothiazolyl substituted with lower alkyl(preferably methyl) (e.g., 3-methylisothiazol-5-yl, etc.); thiazolidinyl(e.g., thiazolidin-2-yl, etc.); thiazolidinyl substituted with loweralkyl (e.g., 3-methylthizolidin-2-yl, etc.), etc.

The alkyl represented by R⁴ includes the above alkyl represented by R².

The alkoxy represented by R⁴ includes, for example, alkoxy having 1 to 6carbon atoms, preferably 1 to 4 carbon atoms, such as methoxy, ethoxy,propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, etc.

The halogen represented by R⁴ includes, for example, fluorine, chlorine,bromine, and iodine.

The halogenated alkyl represented by R⁴ includes the above alkylrepresented by R² which is substituted with at least one halogen (e.g.,fluorine, chlorine, bromine, iodine), such as trifluoromethyl, etc.

R⁴ is preferably hydrogen.

The alkyl and acyl represented by R¹⁶ include the above alkyl and acylrepresented by R⁹ or R¹⁰, respectively.

M is preferably an oxygen atom, sulfur atom or NR¹⁶, more preferably anoxygen atom.

When R³ is imidazol-1-yl or 1,2,4-triazol-1-yl, n is 1.

The compound of the present invention has two kinds of isomers: E and Zisomers. The present invention includes these isomers and mixtures ofthe isomers in any mixing ratios. This is herein indicated by the waveline (˜) in the formulas.

In addition, the compound of the present invention includes itshydrochloric acid salt, sulfuric acid salt, nitric acid salt, oxalicacid salt and p-toluenesulfonic acid salt.

Specific examples of the compound of the formula (I) of the presentinvention include compounds described in Examples hereinafter.Particularly preferred are the compounds of the formula (I) wherein

R¹ is phenyl, R² is methyl, R³ is imidazol-1-yl, R⁴ is hydrogen, and nis 1 (Compound No. 1: Compound Nos. correspond to those in Exampleshereinafter);

R¹ is 4-chlorophenyl, R² is methyl, R³ is imidazol-1-yl, R⁴ is hydrogen,and n is 1 (Compound No. 7);

R¹ is 2-methylphenyl, R² is methyl, R³ is imidazol-1-yl, R⁴ is hydrogen,and n is 1 (Compound No. 13);

R¹ is 4-methylphenyl, R² is methyl, R³ is imidazol-1-yl, R⁴ is hydrogen,and n is 1 (Compound No. 15);

R¹ is 2-ethylphenyl, R² is methyl, R³ is imidazol-1-yl, R⁴ is hydrogen,and n is 1 (Compound No. 16);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is imidazol-1-yl, R⁴ ishydrogen, and n is 1 (Compound No. 39);

R¹ is phenyl, R² is ethyl, R³ is imidazol-1-yl, R⁴ is hydrogen, and n is1 (Compound No. 61);

R¹ is phenyl, R² is allyl, R³ is imidazol-1-yl, R⁴ is hydrogen, and n is1 (Compound No. 81);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is 1-methylimidazol-2-yl, R⁴is hydrogen, and n is 1 (Compound No. 136);

R¹ is 4-chloro-2-methylphenyl, R² is methyl, R³ is1-methylimidazol-2-yl, R⁴ is hydrogen, and n is 1 (Compound No. 141);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is isoxazol-3-yl, R⁴ ishydrogen, and n is 1 (Compound No. 336);

R¹ is 5-trifluoromethylpyridin-2-yl, R² is methyl, R³ is isoxazol-3-yl,R⁴ is hydrogen, and n is 1 (Compound No. 387);

R¹ is 5-trifluoromethyl-3-chloropyridin-2-yl, R² is methyl, R³ isisoxazol-3-yl, R⁴ is hydrogen, and n is 1 (Compound No. 390);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is 5-methylisoxazol-3-yl, R⁴is hydrogen, and n is 1 (Compound No. 436);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is 3-methylisoxazol-5-yl, R⁴is hydrogen, and n is 1 (Compound No. 636);

R¹ is 5-trifluoromethyl-3-chloropyridin-2-yl, R² is methyl, R³ is3-methylisoxazol-5-yl, R⁴ is hydrogen, and n is 1 (Compound No. 690);

R¹ is 2-methylphenyl, R² is methyl, R³ is 1,3,4-oxadiazol-2-yl, R⁴ ishydrogen, and n is 1 (Compound No. 712);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is 1,3,4-oxadiazol-2-yl, R⁴is hydrogen, and n is 1 (Compound No. 736);

R¹ is 4-chloro-2-methylphenyl, R² is methyl, R³ is 1,3,4-oxadiazol-2-yl,R⁴ is hydrogen, and n is 1 (Compound No. 741);

R¹ is 4-chlorophenyl, R² is methyl, R³ is 1,2,4-oxadiazol-3-yl, R⁴ ishydrogen, and n is 1 (Compound No. 807);

R¹ is 2-methylphenyl, R² is methyl, R³ is 1,2,4-oxadiazol-3-yl, R⁴ ishydrogen, and n is 1 (Compound No. 812);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is 1,2,4-oxadiazol-3-yl, R⁴is hydrogen, and n is 1 (Compound No. 836);

R¹ is 2-methylphenyl, R² is methyl, R³ is 5-methyl-1,2,4-oxadiazol-3-yl,R⁴ is hydrogen, and n is 1 (Compound No. 912);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is5-methyl-1,2,4-oxadiazol-3-yl, R⁴ is hydrogen, and n is 1 (Compound No.936);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is1-methyl-2-imidazolin-2-yl, R⁴ is hydrogen, and n is 1 (Compound No.1136);

R¹ is 4-chlorophenyl, R² is methyl, R³ is 1,2,4-oxadiazol-5-yl, R⁴ ishydrogen, and n is 1 (Compound No. 1584);

R¹ is 2,5-dimethylphenyl, R² is methyl, R³ is 2-methyl-2H-tetrazol-5-yl,R⁴ is hydrogen, and n is 1 (Compound No. 2036);

R¹ is 3,5-dichloropyridin-2-yl, R² is methyl, R³ is isoxazol-3-yl, R⁴ ishydrogen, and n is 1 (Compound No. 2276);

R¹ is 5-chloro-3-trifluoromethylpyridin-2-yl, R² is methyl, R³ isisoxazol-3-yl, R⁴ is hydrogen, and n is 1 (Compound No. 2306);

R¹ is a group represented by the formula (a), R⁹ is 4-chlorophenyl, R¹⁰is methyl, R² is methyl, R³ is isoxazol-3-yl, R⁴ is hydrogen, and n is 1(Compound No. 2387);

R¹ is a group of by the formula (a), R⁹ is 3-trifluoromethylphenyl, R¹⁰is methyl, R² is methyl, R³ is isoxazol-3-yl, R⁴ is hydrogen, and n is 1(Compound No. 2399);

R¹ is a group of the formula (a), R⁹ is 3,4-dichlorophenyl, R¹⁰ ismethyl, R² is methyl, R³ is isoxazol-3-yl, R⁴ is hydrogen, and n is 1(Compound No. 2408);

R¹ is a group represented by the formula (a), R⁹ is 4-chlorophenyl, R¹⁰is methyl, R² is methyl, R³ is 3-methylisoxazol-5-yl, R⁴ is hydrogen,and n is 1 (Compound No. 2507);

R¹ is a group of the formula (a), R⁹ is 3-trifluoromethylphenyl, R¹⁰ ismethyl, R² is methyl, R³ is thiazolidin-2-yl, R⁴ is hydrogen, and n is 1(Compound No. 2799) ; or

R¹ is a group of the formula (a), R⁹ is 3-trifluoromethylphenyl, R¹⁰ ismethyl, R² is methyl, R³ is 3-methylthiazolidin-2-yl, R⁴ is hydrogen,and n is 1 (Compound No. 2839).

The compound (I) (i.e., the compound of the formula (I); hereinafter thecompounds of other formulas are sometimes abbreviated likewise) can beprepared, for example, according to the following synthetic routes.

[Route 1]

wherein A is halogen (e.g., chlorine, bromine, iodine, etc.), and theother symbols are as defined above.

The compound of the formula (IV) can be prepared by reacting thecompound (IIa) with the compound (III) or a salt thereof (e.g.,hydrochloric acid salt, sulfuric acid salt) in the presence of a base inthe absence of a solvent or in an appropriate solvent (alone or as amixture).

In this reaction, the amount of the compound (III) to be used is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(IIa).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), amines(e.g., pyridine, triethylamine, etc.), etc. The amount of the base to beused is 1 equivalent or more, preferably 1 to 3 equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), ethers (e.g.,tetrahydrofuran (THF), dioxane, etc.), water, mixtures thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 48 hours.

The compound (IV) thus obtained can be used in the next step as thecrude product or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

The acid halide (IIa) used as the starting material in this reaction canbe prepared according to JP-A 5-331124, for example, by halogenating thecorresponding carboxylic acid with a thionyl halide (e.g., thionylchloride, etc.), phosphoryl halide (e.g., phosphoryl chloride, etc.),phosgene, etc.

[Route 1 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (V) can be prepared by reacting the abovecompound (IV) with a halogenating agent in the absence of a solvent orin an appropriate solvent (alone or as a mixture).

Examples of the halogenating agent to be used include thionyl halides(e.g., thionyl chloride, thionyl bromide, etc.), phosphoryl halides(e.g., phosphoryl chloride, phosphoryl bromide, etc.), phosphorushalides (e.g., phosphorus pentachloride, phosphorus trichloride,phosphorus pentabromide, phosphorus tribromide, etc.), phosgene, oxalylhalides (e.g., oxalyl chloride, etc.), triphenylphosphine/carbontetrachloride, triphenylphosphine/carbon tetrabromide, etc. The amountof the halogenating agent to be used is 1 equivalent or more, preferably1 to 4 equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), nitriles (e.g.,acetonitrile, etc.), mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to120° C. The reaction time varies with the kind of compound, and is 0.1to 48 hours.

The compound (V) thus obtained can be used in the next step as the crudeproduct or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 1 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (VII) can be prepared by reacting thecompound (VI) with the compound (III) or a salt thereof (e.g.,hydrochloric acid salt, sulfuric acid salt) in the presence of a base inthe absence of a solvent or in an appropriate solvent (alone or as amixture).

The amount of the compound (III) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(VI).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), amines(e.g., pyridine, triethylamine, etc.), etc. The amount of the base to beused is 1 equivalent or more, preferably 1 to 3 equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane,etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 48 hours.

The compound (VII) thus obtained can be used in the next step as thereaction mixture or the crude product or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

The compound (VI) used as the starting material in this reaction can beprepared according to Takahashi et al. Tetrahedron Letters 22 (28),2651-2654 (1981), for example, by halogenating the correspondingphthalide with triphenyl-phosphine dichloride, etc.

[Route 1 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (VIII) can be prepared by reacting thecompound (VII) with a halogenating agent in the absence of a solvent orin an appropriate solvent (alone or as a mixture).

Examples of the halogenating agent to be used include thionyl halides(e.g., thionyl chloride, thionyl bromide, etc.), phosphoryl halides(e.g., phosphoryl chloride, phosphoryl bromide, etc.), phosphorushalides (e.g., phosphorus pentachloride, phosphorus trichloride, etc.),phosgene, and oxalyl halides (e.g., oxalyl chloride, etc.). The amountof the halogenating agent to be used is 1 equivalent or more, preferably1 to 2 equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to120° C. The reaction time varies with the kind of compound, and is 0.1to 48 hours.

The compound (VIII) thus obtained can be used in the next step as thecrude product or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 1 (Continued)]

(Scheme 5)

wherein each symbol is as defined above.

The compound of the formula (Va) can be prepared by reacting thecompound (VIII) with the compound (IX) in the presence of a base in theabsence of a solvent or in an appropriate solvent (alone or as amixture).

The amount of the compound (IX) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(VIII).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 3equivalents.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitrites (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 120 hours.

The compound (Va) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 1 (Continued)]

wherein each symbol is as defined above, and, in this reaction, R³ ispreferably pyrrolyl (e.g., pyrrol-1-yl, etc.), imidazolyl (e.g.,imidazol-1-yl, etc.), pyrazolyl (e.g., pyrazol-1-yl, etc.) or triazolyl(e.g., 1H-1,2,4-triazol-1-yl, etc.).

The compound of the formula (I) of the present invention can be preparedby reacting the compound (V) with the compound (X) in the presence orabsence of a base in the absence of a solvent or in an appropriatesolvent (alone or as a mixture).

The amount of the compound (X) to be used in this reaction is 1equivalent or more, preferably 1 to 5 equivalents, based on the compound(V).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal hydrides (e.g., sodiumhydride, etc.), metal carbonates (e.g., sodium carbonate, potassiumcarbonate, etc.), metal alkoxides (e.g., sodium methoxide, sodiumethoxide, potassium tert-butoxide, etc.), amines (e.g., pyridine,triethylamine, etc.), etc. The amount of the base to be used is 1equivalent or more, preferably 1 to 5 equivalents.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethate, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitrites (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 170° C., preferably −10° C. to140° C. The reaction time varies with the kind of compound, and is 0.5to 80 hours.

If necessary, the desired compound (I) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 2]

wherein Z is lithium or magnesium halide (e.g., -MgBr, -MgI, etc.), L ishalogen (e.g., chlorine, bromine, iodine, etc.), alkoxy (e.g., loweralkoxy such as methoxy, ethoxy, propoxy, etc.), imidazol-1-yl orN-methyl-N-methoxyamino, R³ is an optionally substituted heterocyclicgroup, and the other symbols are as defined above.

The compound of the formula (XIV) can be prepared by reacting thecompound (XI) with the compound (XII) or (XIII) in an appropriatesolvent (alone or as a mixture).

The amount of the compound (XII) or (XIII) to be used in this reactionis 1 equivalent or more, preferably 1 to 3 equivalents, based on thecompound (XI).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, diethyl ether, dioxane,etc.), triethylamine, mixed solvents thereof, etc.

The reaction temperature is −100° C. to 100° C., preferably −80° C. to40° C. The reaction time varies with the kind of compound, and is 0.5 to80 hours.

The compound (XIV) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

The compound (XI) used as the starting material in this reaction can beprepared according to JP-A 3-246268 or JP-A 5-97768, for example, byreacting a compound corresponding to the compound (XI) wherein themoiety Z is halogen with butyl lithium or magnesium.

[Route 2 (Continued)]

(Scheme 8)

wherein each symbol is as defined above.

The compound of the formula (XIV) can be prepared by reacting thecompound (II) with the compound (XV) in an appropriate solvent (alone oras a mixture).

The amount of the compound (XV) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(II).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, diethyl ether, dioxane,etc.), triethylamine, mixed solvents thereof, etc.

The reaction temperature is −100° C. to 100° C., preferably −80° C. to40° C. The reaction time varies with the kind of compound, and is 0.5 to80 hours.

The compound (XIV) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

The compound (XV) can be prepared by reference to A. R. Katritzky,Handbook of Heterocyclic Chemistry, 360-361 (1985), for example, bylithiating the corresponding heterocyclic compound with butyl lithium,etc., or by reacting the corresponding halogenated heterocyclic compoundwith magnesium.

[Route 2 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (I) of the present invention can be preparedby reacting the compound (XIV) with the compound (III) or a salt thereof(e.g., hydrochloric acid salt, sulfuric acid salt) in an appropriatesolvent (alone or as a mixture).

The amount of the compound (III) to be used in this reaction is 1equivalent or more, preferably 1 to 4 equivalents, based on the compound(XIV).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), alcohols (e.g., methanol, ethanol, propanol,etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 160° C., preferably 60° C. to 130°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

If necessary, the desired compound (I) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 2 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (XVI) can be prepared by reacting thecompound (XIV) with hydroxylamine or a salt thereof (e.g., hydrochloricacid salt, sulfuric acid salt) in an appropriate solvent (alone or as amixture).

The amount of the hydroxylamine or a salt thereof to be used in thisreaction is 1 equivalent or more, preferably 1 to 4 equivalents, basedon the compound (XIV).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), alcohols (e.g., methanol, ethanol, propanol,etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 160° C., preferably 60° C. to 130°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

The compound (XVI) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 2 (Continued)]

wherein Y is halogen (e.g., chlorine, bromine, iodine, etc.),alkylsulfonyloxy (e.g., lower alkylsulfonyloxy such asmethylsulfonyloxy, ethylsulfonyloxy, etc.) or alkoxysulfonyloxy (e.g.,lower alkoxysulfonyloxy such as methoxysulfonyloxy, ethoxysulfonyloxy,etc.), and the other symbols are as defined above.

The compound of the formula (I) of the present invention can be preparedby reacting the compound (XVI) with the compound (XVII) in the presenceof a base in an appropriate solvent (alone or as a mixture).

The amount of the compound (XVII) to be used in this reaction is 1equivalent, preferably 1 to 2 equivalents, based on the compound (XVI).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 90 hours.

If necessary, the desired compound (I) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 3]

wherein R⁵ is hydrogen or alkyl (e.g., lower alkyl such as methyl,ethyl, propyl, etc.), and the other symbols are as defined above.

The compound of the formula (XX) can be prepared by reacting thecompound (XVIII) with the compound (XIX) in the absence of a solvent orin an appropriate solvent (alone or as a mixture), for example, byreference to Y. Lin et al., J. Org. Chem., 44, 4160 (1979).

The amount of the compound (XIX) to be used in this reaction is 1equivalent or more, preferably 1 to 5 equivalents, based on the compound(XVIII).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, diethyl ether, dioxane,etc.), mixed solvents thereof, etc.

The reaction temperature is 0° C. to 180° C., preferably 20° C. to 120°C. The reaction time varies with the kind of compound, and is 0.5 to 80hours.

The compound (XX) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

The compound (XVIII) used as the starting material in this reaction canbe prepared, for example, according to JP-A 3-246268 or JP-A 5-97768,for example, by reacting the corresponding carboxylic acid ester withammonia or by subjecting the corresponding α-ketoamide to oximation.

[Route 3 (Continued)]

(Scheme 13)

wherein R⁶ is hydrogen or alkyl (e.g., lower alkyl such as methyl,ethyl, propyl, etc.), and the other symbols are as defined above.

The compound of the formula (Ia) of the present invention can beprepared by reacting the compound (XX) with the compound (XXI) in thepresence of an acid in the absence of a solvent or in an appropriatesolvent (alone or as a mixture) by reference to Y. Lin et al., J. Org.Chem., 44, 4160 (1979).

The amount of the compound (XXI) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(XX).

Examples of the acid to be used include aliphatic carboxylic acids(e.g., acetic acid, etc.). The amount of the acid to be used is 1equivalent or more, preferably 5 to 50 equivalents, based on thecompound (XX).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is 0° C. to 180° C., preferably 20° C. to 120°C. The reaction time varies with the kind of compound, and is 0.5 to 80hours.

If necessary, the desired compound (Ia) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 4]

wherein each symbol is as defined above.

The compound of the formula (XXII) can be prepared by reacting thecompound (XX) with hydroxylamine in the presence of an acid in theabsence of a solvent or in an appropriate solvent (alone or as amixture) by reference to Y. Lin et al., J. Org. Chem., 44, 4160 (1979).

The amount of the hydroxylamine to be used in this reaction is 1equivalent or more, preferably 1 to 3 equivalents, based on the compound(XX).

Examples of the acid to be used include aliphatic carboxylic acids(e.g., acetic acid, etc.). The amount of the acid to be used is 1equivalent or more, preferably 5 to 50 equivalents, based on thecompound (XX).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, dioxane, etc.), water,mixed solvents thereof, etc.

The reaction temperature is −10° C. to 120° C., preferably 0° C. to 80°C. The reaction time varies with the kind of compound, and is 0.1 to 40hours.

The compound (XXII) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 4 (Continued)]

(Scheme 15)

wherein each symbol is as defined above.

The compound of the formula (Ib) of the present invention can beprepared by subjecting the compound (XXII) to ring closure reaction inthe presence of an acid in the absence of a solvent or in an appropriatesolvent (alone or as a mixture) by reference to Y. Lin et al., J. Org.Chem., 44, 4160 (1979).

Examples of the acid to be used include aliphatic carboxylic acids(e.g., acetic acid, etc.). The amount of the acid to be used is 1equivalent or more, preferably 5 to 50 equivalents, based on thecompound (XXII).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is 20° C. to 180° C., preferably 50° C. to 140°C. The reaction time varies with the kind of compound, and is 0.5 to 80hours.

If necessary, the desired compound (Ib) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 5]

wherein each symbol is as defined above.

The compound of the formula (Ib) of the present invention can beprepared by reacting the compound (XXIII) with the compound (XXIV) inthe presence of a base in the absence of a solvent or in an appropriatesolvent (alone or as a mixture) by reference to S. Chiou et al., J.Heterocyclic Chem., 26, 125 (1989).

The amount of the compound (XXIV) to be used in this reaction is 1equivalent or more, preferably 1 to 3 equivalents, based on the compound(XXIII).

Examples of the base to be used include amines (e.g., pyridine,triethylamine, etc.). The amount of the base to be used is 1 equivalentor more, preferably 3 to 20 equivalents, based on the compound (XXIII).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is 20° C. to 180° C., preferably 50° C. to 140°C. The reaction time varies with the kind of compound, and is 0.5 to 80hours.

If necessary, the desired compound (Ib) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compound (XXIII) used as the starting material in this reaction canbe prepared, for example, according to Japanese Patent Application No.5-56143, for example, by subjecting the correspondingα-methoxyimino(substituted)-benzyl cyanide to hydrolysis with a base(e.g., sodium hydroxide, potassium hydroxide, etc.) to give a carboxylicacid, and then halogenating the carboxylic acid with a thionyl halide(e.g., thionyl chloride, etc.), phosphoryl halide (e.g., phosphorylchloride, etc.), etc.

[Route 6]

wherein R⁷ is alkyl (e.g., lower alkyl such as methyl, ethyl, propyl,etc.), and the other symbols are as defined above.

The compound of the formula (XXVI) can be prepared by reacting thecompound (XXV) with a monohydrate of the compound (XXIa) or a saltthereof (e.g., hydrochloric acid salt, sulfuric acid salt) in anappropriate solvent (alone or as a mixture).

The amount of the compound (XXIa) to be used in this reaction is 1equivalent or more, preferably 1 to 5 equivalents, based on the compound(XXV).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), alcohols (e.g., methanol, ethanol, propanol,etc.), ethers (e.g., THF, dioxane, etc.), water, mixed solvents thereof,etc.

The reaction temperature is 0° C. to 160° C., preferably 10° C. to 130°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

The compound (XXVI) thus obtained can be used in the next. step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

The compound (XXV) used as the starting material in this reaction can beprepared, for example, according to JP-A 4-295454, for example, bysubjecting the corresponding α-ketocarboxylic acid ester or a ketal atthe α-position of the ester to oximation.

[Route 6 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (Ic) of the present invention can beprepared by reacting the compound (XXVI) with the compound (XXVII) inthe absence of a solvent or in an appropriate solvent (alone or as amixture) by reference to C. Ainaworth, J. Am. Chem. Soc., 77, 1148(1955).

The amount of the compound (XXVII) to be used in this reaction is 1equivalent or more, preferably 1 to 20 equivalents, based on thecompound (XXVI).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is 20° C. to 200° C., preferably 50° C. to 170°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

If necessary, the desired compound (Ic) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 7]

wherein each symbol is as defined above.

The compound of the formula (XXIX) can be prepared by reacting thecompound (XXVIII) with hydroxylamine or a salt thereof (e.g.,hydrochloric acid salt, sulfuric acid salt) in the presence or absenceof a base in an appropriate solvent (alone or as a mixture).

The amount of the hydroxylamine or a salt thereof to be used in thisreaction is 1 equivalent or more, preferably 1 to 3 equivalents, basedon the compound (XXVIII).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, etc.), amines (e.g., pyridine,triethylamine, etc.), etc. The amount of the base to be used is 1equivalent or more, preferably 1 to 2 equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), alcohols (e.g., methanol, ethanol, propanol,etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 160° C., preferably 20° C. to 110°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

The compound (XXIX) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

The compound (XXVIII) used as the starting material in this reaction canbe prepared, for example, according to Route 13, 14 or 15, or JapanesePatent Application No. 4-324120, for example, by introducing the cyanomoiety to the corresponding (substituted)benzyl halide using an alkalinemetal cyanide (e.g., sodium cyanide, etc.), and then subjecting theresulting compound to oximation. [Route 7 (Continued)]

wherein each symbol is as defined above except that R⁵ of the compound(XXX) is other than hydrogen and preferably lower alkyl such as methyl,ethyl, propyl, etc.

The compound of the formula (Id) of the present invention can beprepared by reacting the compound (XXIX) with the compound (XXVII) or(XXX) in the absence of a solvent or in an appropriate solvent (alone oras a mixture) by reference to U.S. Pat. No. 3,910,942.

The amount of the compound (XXVII) or (XXX) to be used in this reactionis 1 equivalent or more, preferably 1 to 20 equivalents, based on thecompound (XXIX).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is 40° C. to 200° C., preferably 60° C. to 180°C. The reaction time varies with the kind of compound, and is 0.5 to 120hours.

If necessary, the desired compound (Id) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compounds of the formulas (Ie), (If) and (Ig) of the presentinvention can be prepared according to the following Route 8.

[Route 8]

wherein each symbol is as defined above.

The compound of the formula (Ie) of the present invention can beprepared by reacting the compound (XXVIII) with an azide compound in thepresence of ammonium chloride in an appropriate solvent (alone or as amixture) by reference to K. Kubo, J. Med. Chem., 36, 2182 (1993).

Examples of the azide compound to be used include alkaline metal azides(e.g., sodium azide, potassium azide, etc.), etc. The amount of theazide compound to be used is 1 equivalent or more, preferably 1 to 15equivalents, based on the compound (XXVIII). The amount of the ammoniumchloride to be used is 1 equivalent or more, preferably 1 to 15equivalents, based on the compound (XXVIII).

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), ethers (e.g., dioxane, etc.), mixed solventsthereof, etc.

The reaction temperature is 40° C. to 200° C., preferably 60° C. to 180°C. The reaction time varies with the kind of compound, and is 0.5 to 120hours.

The desired compound (Ie) thus obtained can be used in the next step asthe reaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 8 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (If) or (Ig) of the present invention can beprepared by reacting the compound (Ie) with the compound (XXXI) in thepresence of a base in an appropriate solvent (alone or as a mixture).

The amount of the compound (XXXI) be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(Ie).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 3equivalents.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 90 hours.

If necessary, the desired compound (If) and (Ig) thus obtained can bepurified by a conventional method (e.g., chromatography,recrystallization, etc.).

The compounds of the formulas (Ih) and (Ii) of the present invention canbe prepared according to the following Route 9.

[Route 9]

wherein each symbol is as defined above.

The compound of the formula (XXXII) can be prepared by reacting thecompound (XXVIII) with methanol in the presence of an acid by referenceto, for example, JP-A 5-271223.

The amount of the methanol to be used in this reaction is 1 equivalentor more, preferably 1 to 1.2 equivalents, based on the compound(XXVIII).

Examples of the acid to be used include hydrochloric acid, hydrobromicacid, etc. The amount of the acid to be used is 1 equivalent or more,preferably 1 to 2 equivalents, based on the compound (XXVIII).

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane,ethyl ether, etc.), mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably 0° C. to 120°C. The reaction time varies with the kind of compound, and is 0.5 to 120hours.

The compound (XXXII) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 9 (Continued)]

(Scheme 24)

wherein each symbol is as defined above.

The compound of the formula (XXXIV) can be prepared by reacting thecompound (XXXII) or a salt thereof (e.g., hydrochloric acid, hydrobromicacid, etc.) with the compound (XXXIII) by reference to, for example,JP-A 5-271223.

The amount of the compound (XXXIII) to be used in this reaction is 1equivalent or more, preferably 1 to 1.2 equivalents, based on thecompound (XXXII).

Examples of the solvent to be used include alcohols (e.g., methanol,ethanol, propanol, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably 0° C. to 120°C. The reaction time varies with the kind of compound, and is 0.5 to 120hours.

The compound (XXXIV) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 9 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (Ih) of the present invention can beprepared by subjecting the compound (XXXIV) or a salt thereof (e.g.,hydrochloric acid, hydrobromic acid, etc.) to ring closure reaction inthe presence of an acid in the absence of a solvent or in an appropriatesolvent (alone or as a mixture) by reference to, for example, JP-A5-271223.

Examples of the acid to be used include hydrochloric acids, hydrobromicacid, etc. The amount of the acid to be used is 1 equivalent or more,preferably 1 to 2 equivalents, based on the compound (XXXIV).

Examples of the solvent to be used include alcohols (e.g., methanol,ethanol, propanol, etc.), ethers (e.g., THF, dioxane, etc.), mixedsolvents thereof, etc.

The reaction temperature is 10° C. to 150° C., preferably 30° C. to 120°C. The reaction time varies with the kind of compound, and is 0.5 to 120hours.

If necessary, the desired compound (Ih) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

[Route 9 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (Ii) of the present invention can beprepared by reacting the compound (Ih) with the compound (XXXI) in thepresence of a base in an appropriate solvent (alone or as a mixture).

The amount of the compound (XXXI) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(Ih).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used is N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 90 hours.

If necessary, the desired compound (Ii) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compound of the formula (Ij) of the present invention can beprepared according to the following Route 10.

[Route 10]

wherein W is oxygen, sulfur or N-R⁵, and R⁵ and the other symbols are asdefined above.

The compound of the formula (Ij) of the present invention can beprepared by reacting the compound (XXVIII) with the compound (XXXV) or asalt thereof (e.g., hydrochloric acid salt, hydrobromic acid salt, etc.)in the presence or absence of a base in the presence or absence of ametal salt in the absence of a solvent or in an appropriate solvent(alone or as a mixture) by reference to Doris P. Schumacher et al., J.Org. Chem., 55, 5291 (1990).

The amount of the compound (XXXV) to be used in this reaction is 1equivalent or more, preferably 1 to 5 equivalents, based on the compound(XXVIII).

Examples of the base to be used include amines (e.g., triethylamine,etc.). The amount of the base to be used is 1 equivalent or more,preferably 1 to 6 equivalents, based on the compound (XXVIII).

Examples of the metal salt to be used include potassium carbonate, zincacetate, etc. The amount of the metal salt to be used is 0.01 to 0.5equivalent, preferably 0.02 to 0.2 equivalent, based on the compound(XXVIII).

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), alcohols(e.g., butanol, 2-methoxyethanol, ethylene glycol, glycerol, etc.),mixed solvents thereof, etc.

The reaction temperature is 20° C. to 200° C., preferably 50° C. to 160°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

If necessary, the desired compound (Ij) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compound of the formula (Ik) of the present invention can beprepared according to the following Route 11.

[Route 11]

wherein each symbol is as defined above.

The compound of the formula (XXXVI) can be prepared by reacting thecompound (XXVIII) or the compound (XXV) with a reducing agent in anappropriate solvent (alone or as a mixture) by reference to, forexample, L.-F Tietze and Th. Eicher, “Reaktionen und Synthesen imorganischchemischen Praktikum”, pp. 84-97 (1981).

Examples of the reducing agent to be used include alkylaluminum hydrides(e.g., diisobutylaluminum hydride, etc.). The amount of the reducingagent to be used is 1 equivalent or more, preferably 1 to 2 equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane,ethyl ether, etc.), mixed solvents thereof, etc.

The reaction temperature is −100° C. to 80° C., preferably −70° C. to30° C. The reaction time varies with the kind of compound, and is 0.5 to120 hours.

The compound (XXXVI) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 11 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (Ik) of the present invention can beprepared by reacting the compound (XXXVI) with the compound (XXXVII) inthe presence of a base in an appropriate solvent (alone or as a mixture)according to, for example, JP-A 58-131984.

The amount of the compound (XXXVII) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(XXXVI).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), alcohols (e.g., methanol, ethanol, propanol,etc.), mixed solvents thereof, etc.

The reaction temperature is 30° C. to 150° C., preferably 50° C. to 100°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

If necessary, the desired compound (Ik) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compound of the formula (In) of the present invention can beprepared according to the following Route 12.

[Route 12]

(Scheme 30)

wherein R⁸ is hydrogen, alkyl (e.g., lower alkyl such as methyl, ethyl,propyl, etc.) or halogen (e.g., fluorine, chlorine, bromine, iodine),and the other symbols are as defined above.

The compound of the formula (XXXIXa) can be prepared by reacting thecompound (XXXVIII) with a Lewis acid in an appropriate solvent (alone ora mixture).

The compound (XXXVIII) is synthesized by a modified method of Routes 1to 11.

Examples of the Lewis acid to be used include aluminium chloride,aluminium bromide, boron trifluoride, boron trichloride, ferricchloride, etc.

The amount of the Lewis acid to be used is 1 equivalent or more,preferably 1 to 3 equivalents, based on the compound (XXXVIII).

Examples of the solvent to be used include anisole, nitromethane,nitroethane, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 120° C., preferably −10° C. to80° C. The reaction time varies with the kind of compound, and is 0.5 to90 hours.

Alternatively, the compound (XXXIXa) can be prepared by reacting thecompound (XXXVIII) with hydrogen in the presence of a catalyst in anappropriate solvent (alone or as a mixture).

The amount of the hydrogen to be used is 1 equivalent or more,preferably 1 to 2 equivalents, based on the compound (XXXVIII).

Examples of the catalyst to be used include palladium-carbon, etc. Theamount of the catalyst to be used is 0.01 equivalent or more, preferably0.01 to 0.2 equivalent, based on the compound (XXXVIII).

Examples of the solvent to be used include ethyl acetate, alcohols(e.g., methanol, ethanol, propanol, etc.), water, mixed solventsthereof, etc.

The reaction temperature is −30° C. to 120° C., preferably −10° C. to80° C. The reaction time varies with the kind of compound, and is 0.5 to90 hours.

The compound (XXXIXa) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 12 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (In) of the present invention can beprepared by reacting the compound (XXXIX) with the compound (XL) in thepresence of a base in an appropriate solvent (alone or as a mixture).

The amount of the compound (XL) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(XXXIX).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used is N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.); halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 190° C., preferably 10° C. to 160°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

If necessary, the desired compound (In) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compound (XXVIII) which can be used as the starting material in theabove Schemes 19, 21, 23, 27 and 28 can be prepared according to thefollowing Route 13, 14 or 15.

[Route 13]

wherein each symbol is as defined above.

The compound of the formula (XXVIII) can be prepared by reacting thecompound (V) with an alkaline metal cyanide (e.g., sodium cyanide,potassium cyanide, etc.) in an appropriate solvent (alone or as amixture).

The amount of the alkaline metal cyanide to be used in this reaction is1 equivalent or more, preferably 1 to 3 equivalents, based on thecompound (V).

Examples of the solvent to be used is N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 190° C., preferably 20° C. to 160°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

The compound (XXVIII) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.

[Route 14]

(Scheme 33)

wherein each symbol is as defined above.

The compound of the formula (XXVIII) can be prepared by reacting thecompound (XVIII) with an acid anhydride in the presence or absence of abase in the absence of a solvent or in an appropriate solvent (alone oras a mixture) by reference to, for example, J. Goto et al., J.Antibiotics, 37, 557 (1984).

Examples of the acid anhydride to be used include acetic anhydride,trifluoroacetic anhydride, etc. The amount of the acid anhydride to beused is 1 equivalent or more, preferably 1 to 5 equivalents, based onthe compound (XVIII).

Examples of the base to be used include amines (e.g., pyridine, etc.),etc. The amount of the base to be used is 1 equivalent or more,preferably 1 to 30 equivalents, based on the compound (XVIII). Examplesof the solvent to be used is aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), mixed solvents thereof, etc.

The reaction temperature is −30° C. to 160° C., preferably −10° C. to110° C. The reaction time varies with the kind of compound, and is 0.5to 90 hours.

The compound (XXVIII) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 15]

wherein R⁴ is as defined above.

The compound of the formula (XLII) can be prepared by reacting thecompound (XLI) with an alkyl nitrite in the presence of a base in anappropriate solvent (alone or as a mixture) in the presence or absenceof a phase-transfer catalyst.

Examples of the alkyl nitrite to be used include methyl nitrite, ethylnitrite, propyl nitrite, isopropyl nitrite, butyl nitrite, isoamylnitrite, etc. The amount of the alkyl nitrite to be used is 1 equivalentor more, preferably 1 to 2 equivalents.

Examples of the phase-transfer catalyst to be used includetetra-n-butylammonium chloride, tetra-n-butylammonium bromide,tetra-n-butylammonium hydrogensulfate, tetramethylammonium bromide,benzyltriethylanmonium chloride, tris(3,6-dioxaheptyl)amine, etc. Theamount of the phase-transfer catalyst to be used is 0.005 to 0.5equivalent, preferably 0.01 to 0.2 equivalent.

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used is N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), alcohols (e.g., methanol, butanol, etc.), water,mixed solvents thereof, etc.

The reaction temperature is −10° C. to 120° C., preferably 0° C. to 80°C. The reaction time varies with the kind of compound, and is 0.5 to 90hours.

The compound (XLII) or a salt thereof (e.g., sodium salt, potassiumsalt, etc.) thus obtained can be used in the next step as the reactionmixture or the crude product, or after purifying it by a conventionalmethod (e.g., chromatography, recrystallization, etc.).

The compound (XLI) used as the starting material in this reaction iscommercially available from Aldrich.

[Route 15 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (XLIII) can be prepared by reacting thecompound (XLII) or a salt thereof (e.g., sodium salt, potassium salt,etc.) with the compound (XVII) in the presence or absence of a base inthe presence or absence of a phase-transfer catalyst in an appropriatesolvent (alone or as a mixture).

The amount of the compound (XVII) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(XLII).

Examples of the phase-transfer catalyst to be used includetetra-n-butylammonium chloride, tetra-n-butylammonium bromide,tetra-n-butylammonium hydrogensulfate, tetramethylammonium bromide,benzyltriethylammonium chloride, tris(3,6-dioxaheptyl)amine, etc. Theamount of the phase-transfer catalyst to be used is 0.005 to 0.5equivalent, preferably 0.01 to 0.2 equivalent.

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used is N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −20° C. to 140° C., preferably 10° C. to120° C. The reaction time varies with the kind of compound, and is 0.5to 90 hours.

The compound (XLIII) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 15 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (XLIV) can be prepared by reacting thecompound (XLIII) with a halogenating agent in the presence of a reactioninitiator in an appropriate solvent (alone or as a mixture).

Examples of the halogenating agent to be used include halogenatedsuccinimide (e.g., N-chlorosuccinimide, N-bromosuccinimide, etc.),chlorine, and bromine. The amount of the halogenating agent to be usedis 1 equivalent or more, preferably 1 to 1.5 equivalent.

Examples of the reaction initiator to be used include peroxides (e.g.,benzoyl peroxide, etc.), azobisisobutyronitrile, etc. The amount of thereaction initiator to be used is 0.01 equivalent or more, preferably0.03 to 0.3 equivalent.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,benzene, etc.), saturated hydrocarbons (e.g., cyclohexane, hexane,etc.), halogenated hydrocarbons (e.g., carbon tetrachloride,1,2-dichloroethane, etc.), mixed solvents thereof, etc.

The reaction temperature is 20° C. to 160° C., preferably 50° C. to 120°C. The reaction time varies with the kind of compound, and is 0.1 to 48hours.

The compound (XLIV) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 15 (Continued)]

(Scheme 37)

wherein each symbol is as defined above.

The compound of the formula (XXVIIIa) can be prepared by reacting thecompound (XLIV) with the compound (IX) in the presence of a base in thepresence or absence of a phase-transfer catalyst in the absence of asolvent or in an appropriate solvent (alone or as a mixture).

The amount of the compound (IX) to be used in this reaction is 1equivalent or more, preferably 1 to 2 equivalents, based on the compound(XLIV).

Examples of the phase-transfer catalyst to be used includetetra-n-butylammonium chloride, tetra-n-butylammonium bromide,tetra-n-butylammonium hydrogensulfate, tetramethylammonium bromide,benzyltriethylammonium chloride, tris(3,6-dioxaheptyl)amine, etc. Theamount of the phase-transfer catalyst to be used is 0.005 to 0.5equivalent, preferably 0.01 to 0.2 equivalent.

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 80 hours.

The compound (XXVIIIa) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

The compound (XXXIX) which can be used as the starting material inScheme 31 described above can also be prepared according to thefollowing Route 16.

[Route 16]

(Scheme 38)

wherein P is a protective group of a hydroxyl group, and the othersymbols are as defined above.

The compound (XLVI) can be prepared by protecting the hydroxyl group ofthe commercially available compound (XLV) with an appropriate protectivegroup.

The hydroxyl group can be protected with a group represented by P by aconventional method for protecting a hydroxyl group described in, forexample, T. W. Green, “Protective Groups in Organic Synthesis”, p.1-113, John Willy & Sons (1981); C. B. Reese, “Protective Groups inOrganic Chemistry”, J. F. Mcomie (ed.), p.95-143, Plenum Press (1973),etc.

For example, the compounds (XLVI) protected with tetrahydropyranyl,tetrahydrothiopyranyl, tetrahydrofuranyl, tetrahydrothiofuranyl,1-ethoxyethyl and 1-methyl-1-methoxyethyl can be prepared by reactingthe compound (XLV) with the corresponding olefins in the presence of anacid catalyst in an appropriate solvent or in the absence of a solvent.

The corresponding olefins are 3,4-dihydro-2H-pyran,2,3-dihydro-4H-thiin, dihydrofuran, dihydrothiofuran, ethyl vinyl ether,and 2-methoxypropene, respectively, and they are commercially availableor can be prepared by known methods.

The amount of the olefin to be used is 1 to 3 equivalents, preferably 1to 2 equivalents, based on the compound (XLV).

Examples of the acid catalyst include hydrogen chloride, phosphorusoxychloride, p-toluenesulfonic acid, p-toluenesulfonic acid pyridinesalt, montmorillonite, bistrimethyl sulfate, acetic acid,p-toluenesulfonic acid polyvinyl pyridinium, trifluoroacetic acid, borontrifluoride etherate (BF₃.OEt₂) and acidic ion-exchange resins, etc.

When a solvent is used, non-alcoholic solvents can be used. Examples ofthe solvent include hydrocarbons (e.g., benzene, toluene, xylene, etc.),halogenated hydrocarbons (e.g., chloroform, dichloromethane, etc.),ethers (e.g., diethyl ether, tetrahydrofuran, dioxane, etc.), esters(e.g., ethyl acetate, etc.), N,N-dimethylformamide, mixed solventsthereof, etc.

The reaction temperature is −30° C. to 100° C., preferably 0° C. to 60°C. The reaction time is normally 15 minutes to 24 hours.

The compound (XLVI) protected with a silyl enol type protective groupcan be obtained by reacting the compound (XLV) with an appropriatesilylating agent. In general, it can be obtained by reacting thecompound (XLV) with chlorosilane in the presence of a base in anappropriate solvent.

Chlorosilane is commercially available or can be prepared by a knownmethod.

The amount of the chlorosilane to be used is 1 to 5 equivalents,preferably 1 to 2 equivalents, based on the compound (XLV).

Examples of the base to be used include organic bases (e.g.,N,N-dimethylaniline, pyridine, triethylamine, imidazole, etc.), metalcarbonates (e.g., sodium carbonate, potassium carbonate, etc.), metalhydrides (e.g., sodium hydride, potassium hydride, etc.), metalbicarbonates (e.g., sodium bicarbonate, potassium bicarbonate, etc.),etc. The amount of the base to be used is 1 equivalent or more,preferably 1 to 2 equivalents.

Examples of the solvent to be used include hydrocarbons (e.g., hexane,benzene, toluene, xylene, etc.), halogenated hydrocarbons (e.g.,chloroform, dichloromethane, etc.), ethers (e.g., diethyl ether,tetrahydrofuran, dioxane, etc.), ketones (e.g., acetone, methyl ethylketone, etc.), nitriles (e.g., acetonitrile, etc.),N,N-dimethylformamide, dimethyl sulfoxide, mixed solvents thereof, etc.

The reaction temperature is −20° C. to 100° C., preferably 0° C. to 60°C.

The reaction time is 5 minutes to 30 hours, preferably 30 minutes to 15hours.

The compound (XLVI) protected with methoxymethyl or triphenylmethyl andthe compound (XLVI) protected with tetrahydrofuranyl or 1-ethoxyethyldescribed above can be obtained by reacting the compound (XLV) with thecorresponding halide in the presence of a base.

The corresponding halides are halomethyl methyl ether, triphenylmethylhalide, 2-halotetrahydrofuran and 1-haloethyl ether, respectively, andthey are commercially available or can be prepared by a known method.

Examples of the halide to be used include chlorides, and bromides.

The amount of the halide to be used, the kind of base and solvent, andthe reaction conditions, etc., are similar to those in the abovereaction of the compound (XLV) with chlorosilane.

Alternatively,the compound (XLVI) protected with methoxymethyl describedabove can also be obtained by reacting the compound (XLV) withdimethoxymethane in the presence of an appropriate catalyst (e.g.,phosphorus pentaoxide, etc.).

The solvent to be used and the reaction conditions are similar to thosein the reaction of the compound (XLV) with olefin.

The compound (XLVI) thus obtained can be used in the next step as thereaction mixture or the crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound (XLVII) can be prepared by reacting the compound (XLVI)with lithium or magnesium in an appropriate solvent.

The amount of the lithium or magnesium to be used is 1 to 4 equivalents,preferably 1 to 2 equivalents, based on the compound (XLVI).

Examples of the solvent to be used include ethers such as dry THF,diethyl ether, dibutyl ether, etc. These solvents can be used alone oras mixtures with other solvents such as hydrocarbons (e.g., toluene,etc.), amines (e.g., triethylamine, etc.), etc.

The reaction temperature is room temperature to 150° C., preferably 40°C. to 100° C.

The reaction time is 10 minutes to 48 hours, preferably 30 minutes to 6hours.

If necessary, as a reaction activating agent, a small amount of iodine,dibromoethane, ethyl bromide, etc., can be used. The amount thereof is0.001 to 0.4 equivalent, preferably 0.005 to 0.2 equivalent.

The compound (XLVII) thus obtained can be used in the next step as thereaction mixture or the crude product.

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (XLVIII) can be prepared by reacting thecompound (XLVII) with the compound (XII) or (XIII) in an appropriatesolvent (alone or as a mixture).

The amount of the compound (XII) or (XIII) to be used in this reactionis 1 equivalent or more, preferably 1 to 3 equivalents, based on thecompound (XLVII).

Examples of the solvent to be used is aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), ethers (e.g., THF, diethyl ether, dioxane,etc.), triethylamine, mixed solvents thereof, etc.

The reaction temperature is −100° C. to 100° C., preferably −80° C. to40° C.

The reaction time varies with the kind of compound, and is 0.5 to 80hours.

The compound (XLVIII) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,chromatography, recrystallization, etc.).

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound (XLIX) can be prepared by reacting the compound (XLVIII)with the compound (III) or a salt thereof in an appropriate solvent.

The amount of the compound (III) to be used is 1 to 4 equivalents,preferably 1 to 2.5 equivalents, based on the compound (XLVIII).

Examples of the salt of the compound (III) include mineral acid saltssuch as a hydrochloric acid salt, sulfuric acid salt, etc. When the saltis used, it is neutralized with a base for the reaction. Examples of thebase to be used include metal hydroxides (e.g., sodium hydroxide,potassium hydroxide, etc.), metal carbonates (e.g., sodium carbonate,potassium carbonate, etc.), metal alkoxides (e.g., sodium methoxide,sodium ethoxide, etc.), etc. The amount of the base to be used is 1 to 3equivalents, preferably 1 to 2 equivalents, based on the compound (III).

Examples of the solvent to be used is hydrocarbons (e.g., benzene,toluene, xylene, etc.), halogenated hydrocarbons (e.g., chloroform,1,2-dichloroethane, etc.), ethers (e.g., tetrahydrofuran, dioxane,etc.), alcohols (e.g., methanol, ethanol, n-propanol, isopropanol,etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 150° C., preferably 20° C. to 100°C.

The reaction time is normally 15 minutes to 24 hours.

The compound (XLIX) thus obtained can be used in the next step as thereaction mixture or crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound (XXXIX) can be obtained by deprotecting the protectivegroup of the hydroxyl group of the compound (XLIX).

The hydroxyl group can be deprotected by a conventional method fordeprotecting a protected hydroxyl group described in, e.g., T. W. Green,“Protective Groups in Organic Synthesis”, p. 1-113, John Willy & Sons(1981); C. B. Reese, “Protective Groups in Organic Chemistry”, J. F.McOmie (ed.), p.95-143, Plenum Press (1973).

For example, the deprotection can be carried out by treating thecompound (XLIX) with an acid when the protective group of the hydroxylgroup is alkyl (e.g., t-butyl, etc.), alkenyl (e.g., allyl, etc.),aralkyl (e.g., triphenylmethyl, etc.), trialkylsilyl (e.g.,t-butyldimethylsilyl, triisopropylsilyl, etc.), alkyldiarylsilyl (e.g.,t-butyldiphenylsilyl, etc.), triaralkylsilyl (e.g., tribenzylsilyl,etc.), alkoxyalkyl (e.g., methoxymethyl, 1-ethoxyethyl,1-methyl-1-methoxyethyl, etc.), alkoxyalkoxyalkyl (e.g.,methoxyethoxymethyl, etc.), alkylthioalkyl (e.g., methylthiomethyl,etc.), tetrahydropyranyl (e.g., tetrahydropyran-2-yl,4-methoxytetrahydropyran-4-yl, etc.), tetrahydrothiopyranyl (e.g.,tetrahydrothiopyran-2-yl, etc.), tetrahydrofuranyl (e.g.,tetrahydrofuran-2-yl, etc.), tetrahydrothiofuranyl (e.g.,tetrahydrothiofuran-2-yl, etc.), aralkyloxyalkyl (e.g., benzyloxymethyl,etc.), etc.

In general, the acid to be used includes, for example, inorganic acidssuch as hydrohalogenic acids (e.g., hydrochloric acid, hydrobromic acid,hydroiodic acid, etc.), hydrogen halides (e.g., hydrogen chloride,hydrogen bromide, hydrogen iodide, etc.), boric acid, phosphoric acid,sulfuric acid, etc., sulfonic acids (e.g., aliphatic sulfonic acids suchas trifluoromethanesulfonic acid, etc., and aromatic sulfonic acids suchas toluenesulfonic acid, etc.), carboxylic acids (e.g., acetic acid,trifluoroacetic acid, etc.), silica gel, Lewis acids [e.g., aluminiumhalides (e.g., aluminium chloride, etc.), zinc chloride, titaniumtetrachloride, etc.], etc. One or more suitable acids can be selectedfrom these acids to use them in the reaction.

The amount of the acid to be used is a trace amount to 1 equivalent.Alternatively, a carboxylic acid can be used as a solvent.

Examples of the solvent to be used is hydrocarbons (e.g., benzene,toluene, xylene, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., tetrahydrofuran, dioxane,etc.), alcohols (e.g., methanol, ethanol, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −80° C. to 150° C., preferably −10° C. to80° C.

The reaction time is 1 minute to 3 hours, preferably 5 minutes to 1hour.

When the protective group is substituted silyl, for example, thedeprotection can be carried out in basic conditions (e.g., sodiumhydroxide/water-containing ethanol, etc.) or in the presence of fluorideion (e.g., n-Bu₄N⁺F⁻, C₅H₅N⁺HF⁻, etc.).

The compound (XXXIX) thus obtained can be used in the next step as thereaction mixture or crude product.

If necessary, the product can be purified by a conventional method(e.g., column chromatography, recrystallization, etc.).

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound (XXXIX) can be prepared by reacting the compound (XLVIII)with the compound (III) or a salt thereof in the presence of a base inan appropriate solvent. The amount of the compound (III) to be used is 1to 4 equivalents, preferably 1 to 2.5 equivalents, based on the compound(XLVIII).

Examples of the salt of the compound (III) include mineral acid saltssuch as a hydrochloric acid salt, sulfuric acid salt, etc. When the saltis used, the salt is neutralized with a base for the reaction.

Examples ot the base to be used include amines (pyridine, etc.), etc.The amount of the base to be used is 1 to 3 equivalents, preferably 1 to2 equivalents, based on the salt of the compound (III).

Examples of the solvent to be used is hydrocarbons (e.g., benzene,toluene, xylene, etc.), halogenated hydrocarbons (e.g., chloroform,1,2-dichloroethane, etc.), ethers (e.g., tetrahydrofuran, dioxane,etc.), alcohols (e.g., methanol, ethanol, n-propanol, isopropanol,etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 150° C., preferably 20° C. to 200°C.

The reaction time is normally 15 minutes to 24 hours.

The compound (XXXIX) thus obtained can be used in the next step as thereaction mixture or crude product, or after purifying it by aconventional method (e.g., column chromatography, recrystallization,etc.).

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound (L) can be prepared by reacting the compound (XLVIII) withhydroxylamine or a salt thereof in an appropriate solvent.

The amount of the hydroxylamine to be used is 1 to 4 equivalents,preferably 1 to 2.5 equivalents, based on the compound (XLVIII).

Examples of the salt of hydroxylamine include mineral acid salts such asa hydrochloric acid salt, sulfuric acid salt, etc. When the salt isused, it is neutralized with a base for the reaction. Examples of thebase to be used include metal hydroxides (e.g., sodium hydroxide,potassium hydroxide, etc.), metal carbonates (e.g., sodium carbonate,potassium carbonate, etc.), metal alkoxides (e.g., sodium methoxide,sodium ethoxide, etc.), etc. The amount of the base to be used is 1 to 3equivalents, preferably 1 to 2 equivalents, based on the salt ofhydroxylamine.

Examples of the solvent to be used include hydrocarbons (e.g., benzene,toluene, xylene, etc.), halogenated hydrocarbons (e.g., chloroform,1,2-dichloroethane, etc.), ethers (e.g., tetrahydrofuran, dioxane,etc.), alcohols (e.g., methanol, ethanol, n-propanol, isopropanol,etc.), water, mixed solvents thereof, etc.

The reaction temperature is 0° C. to 150° C., preferably 20° C. to 100°C.

The reaction time is normally 15 minutes to 24 hours.

The compound (L) thus obtained can be used in the next step as thereaction mixture or crude product, or after purifying it by aconventional method (e.g., column chromatography, recrystallization,etc.).

[Route 16 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (XLIX) can be prepared by reacting thecompound (L) with the compound (XVII) in the presence of a base in anappropriate solvent (alone or as a mixture). The amount of the compound(XVII) to be used in this reaction is 1 equivalent or more, preferably 1to 2 equivalents, based on the compound (L).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more, preferably 1 to 2equivalents.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C.

The reaction time varies with the kind of compound, and is 0.5 to 90hours.

The compound (XLIX) thus obtained can be used in the next step as thereaction mixture or crude product, or after purifying it by aconventional method (e.g., chromatography, recrystallization, etc.).

The compound of the formula (II) of the present invention can beprepared according to the following Route 17.

[Route 17]

wherein V is oxygen, sulfur or N—R⁵, and R⁵ and the other symbols are asdefined above.

The compound of the formula (Ii) of the present invention can beprepared by reacting the compound (XXXVI) with the compound (LI) or asalt thereof (e.g., hydrochloric acid salt, hydrobromic acid salt, etc.)in the presence or absence of a base, or in the presence or absence ofan acid, or in the presence or absence of a metal salt, in the absenceof a solvent or in an appropriate solvent (alone or as a mixture) byreference to, e.g., T. W. Green, “Protective Groups in OrganicSynthesis”, p. 109-151, John Willy & Sons (1981).

The amount of the compound (LI) to be used in this reaction is 1equivalent or more, preferably 1 to 5 equivalents, based on the compound(XXXVI).

Examples of the base to be used include amines (e.g., triethylamine,etc.), etc. The amount of the base to be used is 1 equivalent or more,preferably 1 to 6 equivalents, based on the compound (XXXVI).

Examples of the acid to be used include inorganic acids (e.g.,hydrochloric acid, sulfuric acid, etc.) and sulfonic acids (e.g.,p-toluenesulfonic acid, etc.). The amount of the acid to be used is 0.01to 0.5 equivalent, preferably 0.02 to 0.2 equivalent, based on thecompound (XXXVI).

Examples of the metal salt to be used include potassium carbonate, zincacetate, etc. The amount of the metal salt to be used is 0.01 to 0.5equivalent, preferably 0.02 to 0.2 equivalent, based on the compound(XXXVI).

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), alcohols(e.g., butanol, 2-methoxyethanol, ethylene glycol, glycerol, etc.),mixed solvents thereof, etc.

The reaction temperature is 20° C. to 200° C., preferably 50° C. to 160°C.

The reaction time varies with the kind of compound, and is 0.5 to 90hours.

If necessary, the desired compound (II) thus obtained can be purified bya conventional method (e.g., chromatography, recrystallization, etc.).

The compound of the formula (Im) of the present invention can beprepared, for example, according to the following Route 18.

[Route 18]

wherein each symbol is as defined above.

The compound of the formula (LII) can be prepared by reacting thecompound (XXXIxb) with a halogenating agent in the absence of a solventor in an appropriate solvent (alone or as a mixture).

Examples of the halogenating agent to be used include thionyl halides(e.g., thionyl chloride, thionyl bromide, etc.), phosphoryl halides(e.g., phosphoryl chloride, phosphoryl bromide, etc.), phosphorushalides (e.g., phosphorus pentachloride, phosphorus trichloride,phosphorus pentabromide, phosphorus tribromide, etc.), phosgene, oxalylhalides (e.g., oxalyl chloride, etc.), triphenylphosphine/carbontetrachloride, triphenylphosphine/carbon tetrabromide, etc. The amountof the halogenating agent to be used is 1 equivalent or more.

Examples of the solvent to be used include aromatic hydrocarbons (e.g.,toluene, benzene, xylene, etc.), saturated hydrocarbons (e.g.,cyclohexane, hexane, etc.), halogenated hydrocarbons (e.g.,dichloromethane, 1,2-dichloroethane, etc.), nitriles (e.g.,acetonitrile, etc.), mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to120° C.

The reaction time varies with the kind of compound, and is 0.1 to 48hours.

The compound (LII) thus obtained can be used in the next step as thecrude product, or after purifying it by a conventional method (e.g.,column chromatography, recrystallization, etc.).

[Route 18 (Continued)]

wherein each symbol is as defined above.

The compound of the formula (Im) can be prepared by reacting thecompound (LII) with the compound (IX) in the presence of a base in theabsence of a solvent or in an appropriate solvent (alone or as amixture).

The amount of the compound (IX) to be used in this reaction is 1equivalent or more based on the compound (LII).

Examples of the base to be used include metal hydroxides (e.g., sodiumhydroxide, potassium hydroxide, etc.), metal carbonates (e.g., sodiumcarbonate, potassium carbonate, etc.), metal alkoxides (e.g., sodiummethoxide, sodium ethoxide, potassium tert-butoxide, etc.), etc. Theamount of the base to be used is 1 equivalent or more.

Examples of the solvent to be used include N,N-dimethylformamide (DMF),dimethyl sulfoxide (DMSO), aromatic hydrocarbons (e.g., toluene,benzene, xylene, etc.), saturated hydrocarbons (e.g., cyclohexane,hexane, etc.), halogenated hydrocarbons (e.g., dichloromethane,1,2-dichloroethane, etc.), ethers (e.g., THF, dioxane, etc.), ketones(e.g., acetone, methyl ethyl ketone, etc.), nitriles (e.g.,acetonitrile, etc.), water, mixed solvents thereof, etc.

The reaction temperature is −30° C. to 150° C., preferably −10° C. to100° C. The reaction time varies with the kind of compound, and is 0.5to 120 hours.

If necessary, the desired compound (Im) thus obtained can be purified bya conventional method (e.g., column chromatography, recrystallization,etc.).

The compound of the formula (I) of the present invention is effectiveagainst a wide variety of phytopathogenic fungi on crop plants (e.g.,rice, wheat, barley, rye, corn, common millet, millet, buckwheat,soybean, redbean, peanut, etc.), fruit trees (e.g., citrus fruits,grape, apple, pear, peach, etc.), vegetables (e.g., cucumber, eggplant,tomato, pumpkin, kidney bean, etc.), etc., or seeds thereof. It is alsoeffective against phytopathogenic fungi in soil. The compound of thepresent invention shows potent fungicidal activity particularly againstPyricularia oryzae, Rhizoctonia solani, Erysiphe araminis, Sphaerothecafuliqinea, Erysiphe cichoracearum, Phytorhthora infestans,Pseudoperonospora cubensis, Peronospora manshurica, Plasmopara viticola,Botrytis cinerea of vegetables, grape, etc., Pythium aphanidermatum,Sclerotinia sclerotiorum of buckwheat, soybean, colza, etc., Corticiumrolfsii of soybean, redbean, potato, peanut, etc., Pseudocercosporellaherpotrichoides, of cereals, etc. Therefore, the compound (I) of thepresent invention is useful as fungicides, particularly as agriculturalfungicides.

Application of the compound (I) of the present invention may be made toplants by any conventional procedure such as atomizing, scattering orspreading of the active compound. Application may also be made throughtreatment of seeds of plants, soil where plants grow, soil for seeding,paddy field or water for perfusion with the active compound. Applicationmay be performed before or after the infection with phytopathogenicfungi on plants.

The compound can be used in a conventional formulation form suitable foragricultural fungicides such as solutions, wettable powders, emulsions,suspensions, concentrated liquid preparations, tablets, granules,aerosols, powders, pastes, dusts, etc.

Such formulation form can be prepared in a conventional manner by mixingat least one compound of the present invention with an appropriate solidor liquid carrier(s) and, if necessary, an appropriate adjuvant(s)(e.g., surfactants, spreaders, dispersants, stabilizers, etc.) forimproving the dispersibility and other properties of the activeingredient.

Examples of the solid carriers or diluents include botanical materials(e.g., flour, tobacco stalk powder, soybean powder, walnut-shell powder,vegetable powder, saw dust, bran, bark powder, cellulose powder,vegetable extract residue, etc.), fibrous materials (e.g., paper,corrugated cardboard, old rags, etc.), artificial plastic powders, clays(e.g., kaolin, bentonite, fuller's earth, etc.), talc, other inorganicmaterials (e.g., pyrophyllite, sericite, pumice, sulfur powder, activecarbon, etc.), chemical fertilizers (e.g., ammonium sulfate, ammoniumphosphate, ammonium nitrate, urea, ammonium chloride, etc.), etc.

Examples of the liquid carriers or diluents include water, alcohols(e.g., methanol, ethanol, etc.), ketones (e.g., acetone, ethyl methylketone, etc.), ethers (e.g., diethyl ether, dioxane, cellosolve,tetrahydrofuran, etc.), aromatic hydrocarbons (e.g., benzene, toluene,xylene, methylnaphthalene, etc.), aliphatic hydrocarbons (e.g.,gasoline, kerosene, lamp oil, etc.), esters, nitriles, acid amides(e.g., dimethylformamide, dimethylacetamide, etc.), halogenatedhydrocarbons (e.g., dichloroethane, carbon tetrachloride, etc.), etc.

Examples of the surfactants include alkyl sulfates, alkyl sulfonates,alkylaryl sulfonates, polyethylene glycol ethers, polyhydric alcoholesters, etc.

Examples of the spreaders or dispersants include casein, gelatin, starchpowder, carboxymethyl cellulose, gum arabic, alginic acid, lignin,bentonite, molasses, polyvinyl alcohol, pine oil, agar, etc.

Examples of the stabilizers include PAP (a mixture ofisopropylphosphate), tricresyl phosphate (TCP), tolu oil, epoxidizedoil, surfactants, fatty acids and their esters, etc.

The composition of the present invention may contain other fungicides,insecticides, herbicides or fertilizers in addition to the aboveingredients.

In general, the above composition contains at least one compound of theformula (I) of the present invention in a concentration of 1 to 95% byweight, preferably 2.0 to 80% by weight. The composition can be used assuch or in a diluted form. About 1.0 g to 5 kg/hectare, preferably about10 g to 1000 g/hectare, of the compound of the present invention is usedin a concentration of normally about 1 to 5,000 ppm, preferably about 10to 1,000 ppm.

EXAMPLES

The following Examples and Test Examples further illustrate the presentinvention in detail, but are not to be construed to limit the scopethereof. The ¹H-NMR (CDCl₃) data in Examples were determined at 270 MHzin CDCl₃ using tetramethylsilane as an internal standard and indicatedin δ values (ppm). The coupling constants (J) are indicated in Hz. Inthe data, s is a singlet, d is a doublet, t is a triplet, q is aquartet, m is a multiplet, brs is a broad singlet.

Example 1 Synthesis of α-ethoxyimino-2-phenoxymethylbenzyl chloride

Dichloroethane (50 ml), thionyl chloride (6.54 g, 0.055 mol) anddimethylformamide (0.25 ml) were added to 2-phenoxymethylbenzoic acid(11.41 g, 0.05 mol), and the mixture was stirred at 80° C. for 2 hours.After completion of the reaction, the mixture was concentrated underreduced pressure, and the residue was dissolved in dichloromethane (25ml). The solution was added to a mixture of ethoxyamine hydrochloride(5.85 g, 0.06 mol), pyridine (9.89 g, 0.125 mol) and dry dichloromethane(50 ml) under ice-cooling over 20 minutes, and then the resultingmixture was stirred at room temperature for 2 hours. After completion ofthe reaction, water (200 ml) was added, adjusted to pH<2 with conc.hydrochloric acid, and extracted with dichloromethane. Thedichloromethane layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. Acetonitrile (150 ml),triphenylphosphine (20.98 g, 0.08 mol) and carbon tetrachloride (24.61g, 0.16 mol) were added to the residue, and the mixture was stirredunder reflux for 1.5 hours. After completion of the reaction, themixture was concentrated under reduced pressure, and the residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to giveα-ethoxyimino-2-phenoxymethylbenzyl chloride (13.51 g, 93.2%) as acolorless oil.

¹H-NMR(CDCl₃) δ ppm: 3.14(3H,t,J=6.7), 4.27(2H,q,J=6.7), 5.28(2H,s),6.93-7.70(9H,m).

Synthesis of 1-(α-ethoxyimino-2-phenoxymethyl-benzyl)-1H-1,2,4-triazole

Dimethylformamide (3 ml) and 60% sodium hydride (0.12 g, 3 mmol) wereadded to 1H-1,2,4-triazole (0.20 g, 3 mmol), and the mixture was stirredat room temperature for 10 minutes. Then60-ethoxyimno-2-phenoxymethylbenzyl chloride (0.43 g, 1.5 mmol) wasadded, and the mixture was stirred at 120° C. for 5 hours. Aftercompletion of the reaction, ether (100 ml) was added, and the mixturewas washed with brine (80 ml) twice. The ether layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give1-(α-ethoxyimino-2-phenoxymethylbenzyl)-1H-1,2,4-triazole (0.42 g,86.9%) as colorless crystals. mp. 78.5-80.5° C.

¹H-NMR(CDCl₃) δ ppm: 1.35(3H,t,J=6.7), 4.30 (2H,q,J=6.7), 4.93(2H,s),6.76-7.55(9H,m), 7.94(1H,s), 9.14(1H,s).

Example 2 Synthesis of 2-chloromethyl-α-methoxyiminobenzyl chloride

2-Chloromethylbenzoyl chloride (18.90 g, 0.1 mol) was dissolved indichloromethane (50 ml). The solution was added to a mixture ofmethoxyamine hydrochloride (12.53 g, 0.15 mol), pyridine (19.78 g, 0.25mol) and dry dichloromethane (150 ml) under ice-cooling over 1 hour, andthen the resulting mixture was stirred at 0° C. for 2 hours. Aftercompletion of the reaction, water (300 ml) was added, adjusted to pH<2with conc. hydrochloric acid, and extracted with dichloromethane. Thedichloromethane layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was dissolved indichloromethane (200 ml), and phosphorus pentachloride (20.82 g, 0.1mol) was added under ice-cooling over 5 minutes. The mixture was stirredat 0° C. for 1 hour. After completion of the reaction, saturated aqueoussodium bicarbonate solution (400 ml) was added, and the mixture wasextracted with dichloromethane. The dichloromethane layer was dried overanhydrous magnesium sulfate, concentrated under reduced pressure, andthe residue was purified by silica gel chromatography (ethylacetate/n-hexane) to give 2-chloromethyl-α-methoxyiminobenzyl chloride(18.15 g, 83.2%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 4.12(3H,s), 4.83(2H,s), 7.40-7.62(4H,m).

Synthesis of 2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl chloride

3-Chlorophenol (3.09 g, 0.024 mol), dimethyl-formamide (20 ml) andpotassium carbonate (4.15 g, 0.03 mol) were added to2-chloromethyl-α-methoxyiminobenzyl chloride (4.36 g, 0.02 mol), and themixture was stirred at room temperature for 4 days. After completion ofthe reaction, ether (250 ml) was added, and the mixture was washed withbrine (200 ml) twice. The ether layer was dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to give2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl chloride (5.66 g, 91.2%)as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 4.02(3H,s), 5.25(2H,s), 6.80-7.70(8H,m).

Synthesis of1-[2-(3-chlorophenoxymethyl)-α-methoxy-iminobenzyl]imidazole

Dimethylformamide (3 ml) and 60% sodium hydride (0.16 g, 3.9 mmol) wereadded to imidazole (0.27 g, 3.9 mmol), and the mixture was stirred atroom temperature for 10 minutes. Then,2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl chloride (0.40 g, 1.3mmol) was added, and the mixture was stirred at 110° C. for 2 hours.After completion of the reaction, ether (100 ml) was added, and themixture was washed with brine (80 ml) twice. The ether layer was driedover anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give1-[2-(3-chlorophenoxymethyl)-α-methoxyiminobenzyl]imidazole (0.29 g,65.3%) as colorless crystals. mp. 96.5-97.5° C.

¹H-NMR(CDCl₃) δ ppm: 3.97(3H,s), 5.00(2H,s), 6.63-7.60(10H,m),7.98(1H,s).

According to the same manner as that of the synthesis of theintermediate in Example 1 or 2, various compounds of the formula (V) ofthe present invention, which are intermediates for production of thecompound (I), were synthesized. The compounds thus obtained and theirphysical data are as follows. In the following tables, the physical dataof the compounds obtained in Examples 1 and 2 are also listed.

No R¹ R² n Physical data V-1 C₆H₅ Me 0 ¹H-NMR(CDCl₃) δ ppm : 4.02(3H,s), 6.94- 7.55(9H, m) V-2 C₆H₅ Me 1 ¹H-NMR(CDCl₃) δ ppm : 4.02(3H, s),5.28(2H, s), 6.93-7.69(9H, m) V-3 C₆H₅ Et 1 ¹H-NMR(CDCl₃) δ ppm:1.34(3H, t, J=6.7), 4.27(2H, q, J=6.7), 5.28(2H, s), 6.93-7.70(9H, m)V-4 C₆H₅ Allyl 1 ¹H-NMR(CDCl₃) δ ppm : 4.69-4.72(2H, m), 5.24- 5.38(2H,m), 5.25(2H, s), 5.94-6.08(1H, m), 6.93- 7.71 (9H, m) V-5 2-Cl—C₆H₄ Me 1¹H-NMR(CDCl₃) δ ppm : 4.07(3H, s), 5.37(2H, s), 6.88-7.79(8H, m) V-63-Cl—C₆H₄ Me 1 ¹H-NMR(CDCl₃) δ ppm : 4.02(3H, s), 5.25(2H, s),6.80-7.70(8H, m) V-7 4-Cl—C₆H₄ Me 1 ¹H-NMR(CDCl₃) δ ppm : 4.01(3H, s),5.24(2H, s), 6.85-7.70(8H, m) V-8 2-Me-C₆H₄ Me 1 ¹H-NMR(CDCl₃) δ ppm :2.30(3H, s), 4.03(3H, s), 5.23(2H, s), 6.80-7.70(8H, m) V-9 4-Me-C₆H₄ Me1 ¹H-NMR(CDCl₃) δ ppm : 2.28(3H, s), 4.03(3H, s), 5.25(2H, s), 6.84(2H,d, J=8.5), 7.08(2H, d, J=8.5)  V-10 2-Et-C₆H₄ Me 1 ¹H-NMR(CDCl₃) δ ppm:1.24(3H, t, J=7.3), 2.73(2H, q, J=7.3), 4.05(3H, s), 5.29(2H, s), 6.81-7.70(8H, m)  V-11 2,5-Me₂- Me 1 ¹H-NMR(CDCl₃) δ ppm : 2.25(3H, s),2.30(3H, s), C₆H₃ 4.05(3H, s), 5.26(2H, s), 6.65-7.70(7H, m)  V-122,6-Me₂- Me 1 ¹H-NMR(CDCl₃) δ ppm : 2.28(6H, s), 4.02(3H, s), C₆H₃5.02(2H, s), 6.93-7.62(6H, m), 7.90(1H, d, J=7.9)  V-13 2-Cl- Me 1 mp65-66° C. pyridin-3-yl

Example 3 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl3-methylisoxazol-5-yl ketone

THF (2 ml) and bromoethane (0.1 ml) were added to magnesium (0.49 g,0.02 mol) in a stream of nitrogen, and the mixture was stirred at 50° C.for 10 minutes. Then, a mixture of1-bromo-2-(2,5-dimethylphenoxymethyl)benzene (2.91 g, 0.01 mol) and THF(8 ml) was added at 50 to 60° C. over 30 minutes, and the mixture wasstirred at 50 to 60° C. for 1 hour. After completion of the reaction,the reaction mixture was added to a mixture of3-methylisoxazol-5-carbonyl chloride (1.45 g, 0.01 mol) and THF (15 ml)at −70 to −60° C. over 15 minutes, and then the mixture was stirred at−70 to −60° C. for 0.5 hours. After completion of the reaction,saturated aqueous ammonium chloride solution (150 ml) was added, and themixture was extracted with ether. The ether layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure, andthe residue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from n-hexane to give2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone (0.56g, 17.4%) as colorless crystals. mp. 106-108° C.

¹H-NMR(CDCl₃) δ ppm: 2.13(3H,s), 2.28(3H,s), 2.38(3H,s), 5.28(2H,s),6.66(1H,s), 6.67(1H,d,J=6.7), 6.72(1H,s), 7.00(1H,d,J=7.9),7.46-7.83(4H,m).

Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-ylketone O-methyloxime

n-Propanol (2 ml) and methoxyamine hydrochloride (0.25 g, 3 mmol) wereadded to 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-ylketone (0.33 g, 1 mmol), and the mixture was stirred under reflux for 15hours. After completion of the reaction, water (200 ml) was added, themixture was extracted with dichloromethane. The dichloromethane layerwas dried over anhydrous magnesium sulfate and concentrated underreduced pressure, and the residue was purified by silica gelchromatography (ethyl acetate/n-hexane) to give isomer A (0.18 g, 51.4%,as colorless crystals) and isomer B (0.15 g, 42.8%, as colorlesscrystals) of 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-ylketone O-methyloxime. One of the isomers A and B is the E-isomer and theother is Z-isomer.

Isomer A: mp. 113-114° C.

¹H-NMR(CDCl₃) δ ppm: 2.11(3H,s), 2.25(3H,s), 2.33(3H,s), 4.12(3H,s),4.98(2H,s), 6.51(1H,s), 6.64(1H,d,J=7.3), 6.91(1H,s), 6.97(1H,d,J=7.3),7.38-7.62(4H,m).

Isomer B: mp. 107-108° C.

¹H-NMR(CDCl₃) δ ppm: 2.13(3H,s), 2.24(3H,s), 2.26(3H,s), 4.04(3H,s),4.93(2H,s), 5.99(1H,s), 6.53(1H,s), 6.65(1H,d,J=7.9), 6.99(1H,d,J=7.3),7.21-7.52(3H,m), 7.68(1H,d,J=7.9).

Example 4 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-ylketone

THF (2 ml) and bromoethane (0.1 ml) were added to magnesium (0.49 g,0.02 mol) in a stream of nitrogen, and the mixture was stirred at 50° C.for 10 minutes. Then, a mixture of1-bromo-2-(2,5-dimethylphenoxymethyl)benzene (2.91 g, 0.01 mol) and THF(8 ml) was added at 50 to 60° C. over 30 minutes, and the mixture wasstirred at 50 to 60° C. for 1 hour. After completion of the reaction,the reaction mixture was added to a mixture of 3-cyanoisoxazole (1.45 g,0.015 mol) and THF (15 ml) at 20° C. or lower over 15 minutes, and thenthe mixture was stirred at room temperature for 2 hours. Aftercompletion of the reaction, 2N sulfuric acid (200 ml) was added, and themixture was extracted with ether. The ether layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure, andthe residue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from n-hexane to give2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone (0.20 g, 6.3%)as colorless crystals. mp. 90.5-92° C.

¹H-NMR(CDCl₃) δ ppm: 2.16(3H,s), 2.29(3H,s), 5.32(2H,s), 6.66(1H,s),6.67(1H,d,J=6.7), 6.86(1H,d,J=1.2), 7.00(1H,d,J=7.3), 7.47(1H,t,J=7.3),7.60-8.03(3H,m), 8.50(1H,d,J=1.8).

Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketoneO-methyloxime

n-Propanol (2 ml) and methoxyamine hydrochloride (0.50 g, 6 mmol) wereadded to 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone (0.64g, 2 mmol), and the mixture was stirred under reflux for 17 hours. Aftercompletion of the reaction, water (100 ml) was added, the mixture wasextracted with dichloromethane. The dichloromethane layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure, andthe residue was purified by silica gel chromatography (benzene/n-hexane)to give 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketoneO-methyloxime (a mixture of isomers A/B) (0.55 g, 81.8%) as colorlesscrystals. mp. 104-108° C.

¹H-NMR(CDCl₃) δ ppm: 2.13(2.15) (3H,s), 2.23(2.25) (3H,s),4.01(4.08)(3H,s), 4.95(5.01)(2H,s), 6.52-7.00(4H,m), 7.29-7.64(4H,m),8.39(8.45)(1H,d,J=1.8).

Example 5 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl1-methylpyrazol-5-yl ketone

Dichloroethane (20 ml), thionyl chloride (1.31 g, 0.011 mol) anddimethylformamide (0.1 ml) were added to2-(2,5-dimethylphenoxymethyl)benzoic acid (2.56 g, 0.01 mol), and themixture was stirred under reflux for 2 hours. After completion of thereaction, the reaction mixture was concentrated under reduced pressureto give crude 2-(2,5-dimethylphenoxymethyl)benzoyl chloride. 1.6Mn-butyllithium/n-hexane solution (6.25 ml, 0.01 mol) was added to amixture of 1-methylpyrazole (0.99 g, 0.012 mol) and THF (10 ml) at −70to −60° C. over 15 minutes, and then the mixture was stirred at −70° C.to room temperature for 1 hour. The reaction mixture was cooled to −70°C., and a solution of the crude 2-(2,5-dimethylphenoxymethyl)benzoylchloride in THF (10 ml) was added, and the mixture was stirred at −70°C. for 1 hour. After completion of the reaction, 1N hydrochloric acid(100 ml) was added, and the mixture was extracted with ether. The etherlayer was dried over anhydrous magnesium sulfate and concentrated underreduced pressure, and the residue was purified by silica gelchromatography (ethyl acetate/n-hexane) to give2-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-yl ketone (0.50 g,15.6%) as colorless crystals.

mp. 88-89° C.

¹H-NMR(CDCl₃) δ ppm: 2.04(3H,s), 2.28(3H,s), 4.22(3H,s), 5.23(2H,s),6.50(1H,d,J=2.4), 6.65(1H,s), 6.66(1H,d,J=6.7), 6.97(1H,d,J=7.3),7.38-7.76(4H,m).

Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-ylketone O-ethyloxime

n-Propanol (2 ml) and ethoxyamine hydrochloride (0.18 g, 1.8 mmol) wereadded to 2-(2,5-dimethylphenoxy-methyl)phenyl 1-methylpyrazol-5-ylketone (0.20 g, 0.6 mmol), and the mixture was stirred under reflux for3 days. After completion of the reaction, water (100 ml) was added, andthe mixture was extracted with dichloromethane. The dichloromethanelayer was dried over anhydrous magnesium sulfate and concentrated underreduced pressure, and the residue was purified by silica gelchromatography (ethyl acetate/n-hexane) to give isomer A (0.11 g, 50.4%,as colorless crystals) and isomer B (0.10 g, 45.9%, as colorlesscrystals) of 2-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-ylketone O-ethyloxime.

Isomer A: mp. 74-76° C.

¹H -NMR(CDCl₃) δ ppm: 1.30 (3H, t,J=7.3), 2.13(3H,s), 2.23(3H,s),4.13(3H,s), 4.24(2H,q,J=7.3), 4.95(2H,s), 5.92(1H,d,J=2.4), 6.51(1H,s),6.64(1H,d,J=7.9), 6.99(1H,d,J=7.3), 7.17-7.64(5H,m).

Isomer B: mp. 84-86° C.

¹H-NMR(CDCl₃) δ ppm: 1.33(3H,t,J=6.7), 2.23(3H,s), 2.29(3H,s),3.68(3H,s), 4.29(2H,q,J=6.7), 5.14(2H,s), 6.30(1H,d,J=1.8), 6.58(1H,s),6.68(1H,d,J=7.3), 7.03(1H,d,J=7.3), 7.16-7.47(3H,m), 7.52(1H,d,J=1.8),7.73(1H,d,J=7.9).

According to the same manner as that of the syntheses of theintermediates in Examples 3 to 5, various compounds of the formula (XIV)of the present invention, which are intermediates for production of thecompound (I), were synthesized. The compounds thus obtained and theirphysical data are as follows. In the following tables, the physical dataof the compounds obtained in Examples 3 to 5 are also listed.

No R¹ R³ n Physical data XIV-1  C₆H₅ 1-Me-imidazol- 0 ¹H-NMR(CDCl₃) δppm : 3.94(3H, s), 2-yl 6.92-7.30(7H, m), 7.43(1H, td, J=8.6, 1.8),7.64(1H, dd, J=7.9, 1.8) XIV-2  2,5-Me₂-C₆H₃ 1-Me-imidazol- 1¹H-NMR(CDCl₃) δ ppm : 2.07(3H, s), 2-yl 2.26(3H, s), 4.01(3H, s),5.23(2H, s), 6.00(1H, s), 6.64(1H, d, J=7.3), 6.97(1H, d, J=7.3),7.05(1H, s), 7.19(1H, s), 7.40-7.83(4H, m) XIV-3  C₆H₅ Isoxazol-3-yl 1¹H-NMR(CDCl₃) δ ppm : 5.34(2H, s), 6.85-7.28(6H, m), 7.46(1H, t, J=7.3),7.61(1H, td, J=7.9, 1.2), 7.74(1H, d, J=7.9), 7.99(1H, dd, J=7.3, 1.2),8.50(1H, dd, J=1.2) XIV-4  2-Me-C₆H₄ Isoxazol-3-yl 1 ¹H-NMR(CDCl₃) δ ppm: 2.21 (3H, s), 5.34(2H, s), 6.80-7.14(5H, m), 7.44- 8.02(4H, m),8.49(1H, d, J=1.2) XIV-5  2,5-Me₂C₆H₃ Isoxazol-3-yl 1 mp 90.5-92° C.XIV-6  C₆H₅ 5-Me-isoxazol- 1 ¹H-NMR(CDCl₃) δ ppm : 2.49(3H, s), 3-yl5.34(2H, s), 6.46(1H, d, J=1.2), 6.88- 7.99(9H, m) XIV-7  2,5-Me₂-C₆H₃5-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.17(3H, s), isoxazol-3-yl 2.28(3H, s),2.49(3H, s), 5.32(2H, s), 6.46(1H, s), 6.66-7.02(3H, m), 7.42- 8.00(4H,m) XIV-8  2-Me-C₆H₄ 3-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.18(3H, s),isoxazol-5-yl 2.38(3H, s), 5.30(2H, s), 6.71(1H, s), 6.81-7.80(8H, m)XIV-9  2,5-Me₂-C₆H₃ 3-Me- 1 mp 106-108° C. isoxazol-5-yl XIV-102,5-Me₂-C₆H₃ 2-isoxazolin- 1 ¹H-NMR(CDCl₃) δ ppm : 2.17(3H, s), 3-yl2.31(3H, s), 3.20(2H, t, J=11.0), 4.42(2H, t, J=11.0), 5.20(2H, s),6.68- 7.84(7H, m) XIV-11 2,5-Me₂-C₆H₃ 5,5-Me₂-2- 1 ¹H-NMR(CDCl₃) δ ppm:1.35(6H, s), isoxazolin-3- 2.16(3H, s), 2.30(3H, s), 2.96(2H, s), yl5.22(2H, s), 6.67-7.80(7H, m) XIV-12 2,5-Me₂-C₆H₃ 1-Me- 1 mp 88-89° C.pyrazol-5-yl XIV-13 2,5-Me₂-C₆H₃ 2-Furyl 1 ¹H-NMR(CDCl₃) δ ppm :2.10(3H, s), 2.26(3H, s), 525(2H, s), 6.55- 6.67(3H, m), 6.97(1H, d,J=7.3), 7.06(1H, d, J=3.7), 7.39-7.80(5H, m) XIV-14 2,5-Me₂-C₆H₃Thiazol-2-yl 1 ¹H-NMR(CDCl₃) δ ppm : 2.11(3H, s), 2.27(3H, s), 5.30(2H,s), 6.64(1H, s), 6.65(1H, d, J=2.5), 6.98(1H, d, J=7.9), 7.45-8.10(6H,m) XIV-15 2,5-Me₂-C₆H₃ 3-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.07(3H, s),isothiazol-5- 2.27(3H, s), 2.53(3H, s), 5.25(2H, s), yl 6.60-7.82(8H, m)XIV-16 4-Cl-2-Me-C₆H₃ 5-Me- 1 mp 103-104° C. isoxazol-3-yl XIV-173-Me-C₆H₄ Isoxazol-3-yl 1 ¹H-NMR(CDCl₃) δ ppm : 2.30(3H, s), 5.32(2H,s), 6.66-6.77(3H, m), 6.87(1H, s), 7.12(1H, t, J=7.3), 7.46- 7.76(3H,m), 8.00(1H, d, J=7.9), 8.50(1H, s) XIV-18 4-Me-C₆H₄ Isoxazol-3-yl 1¹H-NMR(CDCl₃) δ ppm : 2.26(3H, s), 5.30(2H, s), 6.77(2H, d, J=8.6),6.86(1H, d, J=1.8), 7.04(2H, d, J=8.6), 7.45-7.98(4H, m), 8.50(1H, d,J=1.8) XIV-19 2-Cl—C₆H₄ Isoxazol-3-yl 1 mp 92.0-93.0° C. XIV-203-Cl—C₆H₄ Isoxazol-3-yl 1 mp 75.0-76.0° C. XIV-21 4-Cl—C₆H₄Isoxazol-3-yl 1 ¹H-NMR(CDCl₃) δ ppm : 5.32(2H, s), 6.80-6.83(2H, m),6.86(1 H, d, J=1.8), 7.19-7.22(2H, m), 7.45-8.02(4H, m), 8.52(1H, d,J=1.2) XIV-22 3-CF₃—C₆H₄ Isoxazol-3-yl 1 ¹H-NMR(CDCl₃) δ ppm : 5.38(2H,s), 6.87(1H, d, J=1.8), 7.04-7.75(7H, m), 8.04(1H, d, J=7.9), 8.52(1H,d, J=1.8) XIV-23 4-Cl-2-Me- Isoxazol-3-yl 1 mp 107.0-108.0° C. C₆H₃XIV-24 2-Me-C₆H₄ 5-Me 1 mp 77.5-78.5° C. isoxazol-3-yl XIV-25 3-Me-C₆H₄5-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.30(3H, s), isoxazol-3-yl 2.49(3H, s),5.32(2H, s), 6.47(1H, d, J=1.2), 6.67-6.85(3H, m), 7.12(1H, t, J=7.3),7.41-7.98(4H, m) XIV-26 4-Me-C₆H₄ 5-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.26(3H,s), isoxazol-3-yl 2.49(3H, s), 5.30(2H, s), 6.46(1H, s), 6.77-6.80(2H,m), 7.05(2H, d, J=7.9), 7.40-7.97(4H, m) XIV-27 2-Cl—C₆H₄ 5-Me- 1 mp93.5-94.5° C. isoxazol-3-yl XIV-28 3-Cl—C₆H₄ 5-Me- 1 mp 72.0-73.0° C.isoxazol-3-yl XIV-29 4-Cl—C₆H₄ 5-Me- 1 mp 95.0-96.0° C. isoxazol-3-ylXIV-30 3-CF₃—C₆H₄ 5-Me- 1 mp 58.5-59.5° C. isoxazol-3-yl XIV-314-Ph—C₆H₄ 5-Me- 1 mp 116.5-117.5° C. isoxazol-3-yl XIV-32 2-Me-C₆H₄Isoxazol-5-yl 1 mp 67.5-68.5° C. XIV-33 2,5-Me₂- Isoxazol-5-yl 1 mp103.5-105.0° C. C₆H₃ XIV-34 4-Cl-2-Me Isoxazol-5-yl 1 mp 109.5-111.0° C.C₆H₃ XIV-35 C₆H₅ 3-Me- 0 ¹H-NMR(CDCl₃) δ ppm : 2.30(3H, s),isoxazol-5-yl 6.76(1H, s), 6.91(1H, d, J=7.3), 6.9- 7.51(7H, m),7.63(1H, dd, J=7.3, 1.8) XIV-36 3-Me-C₆H₄ 3-Me- 1 mp 68.0-69.0° C.isoxazol-5-yl XIV-37 2-Cl—C₆H₄ 3-Me- 1 mp 104.0-105.0° C. isoxazol-5-ylXIV-38 3-Cl—C₆H₄ 3-Me- 1 mp 92.5-93.5° C. isoxazol-5-yl XIV-393-CF₃—C₆H₄ 3-Me- 1 mp 80.5-81.5° C. isoxazol-5-yl XIV-40 4-Cl-2-Me-3-Me- 1 mp 125.5-126.5° C. C₆H₃ isoxazol-5-yl XIV-41 4-Ph—C₆H₄ 3-Me- 1mp 127.0-128.0° C. isoxazol-5-yl XIV-42 C₆H₅ 1-Me- 1 ¹H-NMR(CDCl₃) δ ppm: 4.01(3H, s), imidazol-2-yl 5.24(2H, s), 6.80-6.83(2H, m), 6.91(1H, t,J=7.3)1 7.04(1H, s), 7.18- 7.81(7H, m) XIV-43 2-Me-C₆H₄ 1-Me- 1¹H-NMR(CDCl₃) δ ppm : 2.13(3H, s), imidazol-2-yl 4.01(3H, s), 5.25(2H,s), 6.78-6.85(2H, m), 7.05(1H, s), 7.10(1H, d, J=7.3), 7.18(1H, s),7.39-7.83(4H, m) XIV-44 3-Me-C₆H₄ 1-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.28(3H,s), imidazol-2-yl 4.01(3H, s), 5.21(2H, s), 6.59-6.74(3H, m), 7.04(1H,s), 7.09(1H, t, J=7.9), 7.18(1H, s), 7.39-7.80(4H, m) XIV-45 4-Me-C₆H₄1-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 2.25(3H, s), imidazol-2-yl 4.02(3H, s),5.20(2H, s), 6.69-6.72(2H, m), 6.99-7.02(2H, m), 7.05(1H, s), 7.18(1H,s), 7.38-7.79(4H, m) XIV-46 2-Cl—C₆H₄ 1-Me- 1 mp 87.0-88.0° C.imidazol-2-yl XIV-47 3-Cl—C₆H₄ 1-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 4.03(3H,s), imidazol-2-yl 5.23(2H, s), 6.70(1H, dd, J=8.6, 1.8), 6.82(1H, t,J=1.8), 6.90(1H, dd, J=7.3, 1.2), 7.06(1H, s), 7.13(1H, t, J=7.9),7.19(1H, d, J=1.2), 7.40-7.81(3H, m) XIV-48 4-Cl—-C₆H₄ 1-Me- 1¹H-NMR(CDCl₃) δ ppm : 4.03(3H, S), imidazol-2-yl 5.22(2H, s),6.73-6.78(2H, m), 7.06(1H, s), 7.13-7.59(6H, m), 7.80(1H, dd, J=7.3,1.2) XIV-49 2,4-Cl₂—C₆H₃ 1-Me- 1 mp 141.0-142.0° C. imidazol-2-yl XIV-503,4-Cl₂—C₆H₃ 1-Me- 1 mp 78.0-79.0° C. imidazol-2-yl XIV-51 4-Cl-2-Me-1-Me- 1 mp 101.0-102.0° C. C₆H₃ imidazol-2-yl XIV-52 3-CF₃—C₆H₄ 1-Me- 1¹H-NMR(CDCl₃) δ ppm : 4.01(3H, s), imidazol-2-yl 5.28(2H, s), 6.97-7.61(9H, m), 7.80(1H, dd, J=7.9, 1.8) XIV-53 2-MeO—C₆H₄ 1-Me- 1 mp88.0-89.0° C. imidazol-2-yl XIV-54 3-MeO—C₆H₄ 1-Me- 1 ¹H-NMR(CDCl₃) δppm : 3.74(3H, s), imidazol-2-yl 4.02(3H, s), 5.21(2H, s), 6.38-6.50(3H,m), 7.05(1H, s), 7.11(1H, t, J=7.9), 7.18(1H, s), 7.42-7.79(4H, m)XIV-55 4-F—C₆H₄ 1-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 4.03(3H, s), imidazol-2-yl5.21(2H, s), 6.72-6.95(4H, m), 7.06(1H, s), 7.18(1H, d, J=1.2), 7.42-7.80(4H, m) XIV-56 3-i-Pr—C₆H₄ 1-Me- 1 ¹H-NMR(CDCl₃) δ ppm : 1.20(6H, d,imidazol-2-yl J=7.3), 2.83(1H, sept, J=7.3), 4.00(3H, s), 5.21 (2H, s),6.60-6.80(3H, m), 7.03(1H, s), 7.11-7.79(6H, m) XIV-57 4-Ph—C₆H₄ 1-Me- 1¹H-NMR(CDCl₃) δ ppm : 4.03(3H, s), imidazol-2-yl 5.28(2H, s),6.87-6.90(2H, m), 7.06(1H, s), 7.19(1H, s), 7.28- 7.84(11H, m) XIV-58C₆H₅ 3,5-Me₂- 1 ¹H-NMR(CDCl₃) δ ppm : 2.17(3H, s), isoxazol-4-yl2.25(3H, s), 5.19(2H, s), 6.78-6.82(2H, m), 6.93(1H, t, J=7.3),7.21-7.67(6H, m) XIV-59 2,5-Me₂- 3,5-Me₂- 1 mp 109.0-110.5° C. C₆H₃isoxazol-4-yl XIV-60 2-Me-C₆H₄ 3-Me-2-isoxazolin- 1 ¹H-NMR(CDCl₃) δ ppm: 2.02(3H, s), 5-yl 2.32(3H, s), 3.08(1H, m), 3.53- 3.62(1H, m),5.33-5.46(2H, m), 5.69(1H, dd, J=11.6, 6.7), 6.88(1H, s), 6.91(1H, s),7.15(1H, t, J=8.5), 7.43- 8.01(4H, m) XIV-61 2,5-Me₂- 3-Me-2-isoxazolin-1 mp 88.0-90.0° C. C₆H₃ 5-yl XIV-62 C₆H₅ 4-Me-1,2,3- 1 ¹H-NMR(CDCl₃) δppm : 2.77(3H, s), thiadiazol-5-yl 5.26(2H, s), 6.76(1H, s), 6.79(1H, d,J=1.2), 6.94(1H, t, J=7.3), 7.21- 7.74(6H, m) XIV-63 2,5-Me₂-4-Me-1,2,3- 1 mp 98.5-99.5° C. C₆H₃ thiadiazol-5-yl XIV-64 2-Me-C₆H₄5-Me-2-isoxazolin- 1 3-yl XIV-65 C₆H₅ 5-Me-2-isoxazolin- 1 3-yl XIV-664-Cl—C₆H₄ 5-Me-2-isoxazolin- 1 3-yl XIV-67 3-CF₃—C₆H₄ 5-Me-2-isoxazolin-1 3-yl XIV-68 4-Cl-2-Me- 5-Me-2-isoxazolin- 1 C₆H₃ 3-yl XIV-69 4-Cl—C₆H₄2-Isoxazolin-3-yl 1 XIV-70 3-CF₃—C₆H₄ 2-Isoxazolin-3-yl 1 XIV-714-Cl-2-Me- 2-Isoxazolin-3-yl 1 C₆H₃ XIV-72 2-Me-C₆H₄ 2-Isoxazolin-3-yl 1XIV-73 C₆H₅ 2-Isoxazolin-3-yl 0 XIV-74 C₆H₅ Isoxazol-3-yl 0

Example 6 Synthesis of 2-(4-chlorophenoxymethyl)phenyl1-methyl-1H-1,2,4-triazol-5-yl ketone O-methyloxime

Dimethylformamide dimethylacetal (0.53 g, 4.5 mmol) was added to2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetamide (0.48 g, 1.5mmol), and the mixture was stirred under reduced pressure (ca. 40 mmHg)at 60° C. for 0.5 hours. After completion of the reaction, the mixturewas concentrated under reduced pressure, and a mixture ofmethylhydrazine (0.08 g, 1.8 mmol) and acetic acid (3 ml) was added tothe residue. The mixture was stirred at 90° C. for 1 hour. Aftercompletion of the reaction, ether (150 ml) was added, and the mixturewas washed with saturated aqueous sodium bicarbonate solution (100 ml)twice. The ether layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) and recrystallized fromethyl acetate/n-hexane to give 2-(4-chlorophenoxymethyl)phenyl1-methyl-1H-1,2,4-triazol-5-yl ketone O-methyloxime (0.31 g, 57.9%) ascolorless crystals.

mp. 113-114° C.

¹H-NMR(CDCl₃) δ ppm: 4.01(3H,s), 4.08(3H,s), 4.91(2H,s),6.67-6.70(2H,m), 7.15-7.18(2H,m), 7.26-7.54(4H,m), 7.83(1H,s).

Example 7 Synthesis of2-(4-chlorophenoxymethyl)-N-hydroxyaminomethylene-α-methoxyiminophenylacetamide

Dimethylformamide dimethylacetal (0.53 g, 4.5 mmol) was added to2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetamide (0.48 g, 1.5mmol), and the mixture was stirred under reduced pressure (ca. 40 mmHg)at 60° C. for 0.5 hours. After completion of the reaction, the mixturewas concentrated under reduced pressure, and a mixture of aqueous 50%hydroxylamine solution. (0.20 g, 2 mmol) and acetic acid (3 ml) wasadded to the residue under ice-cooling. The mixture was stirred at roomtemperature for 1 hour. After completion of the reaction, ethyl acetate(150 ml) was added, and the mixture was washed with saturated aqueoussodium bicarbonate solution (100 ml) twice. The ethyl acetate layer wasdried over anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was recrystallized from ethyl acetate/n-hexane togive2-(4-chlorophenoxymethyl)-N-hydroxyaminomethylene-α-methoxyiminophenylacetamide(0.41 g, 75.6%) as colorless crystals.

mp. 185-186° C. (decomposition)

¹H-NMR(CDCl₃) δ ppm: 4.00(3H,s), 4.93(2H,s), 6.76-6.80(2H,m),6.86(1H,d,J=8.5), 7.18-7.22(2H,m), 7.37-7.52(3H,m), 7.70(1H,d,J=10.4),9.50(1H,d,J=9.8).

Synthesis of 2-(4-chlorophenoxymethyl)phenyl 1,2,4-oxadiazol-5-yl ketoneO-methyloxime

Dioxane (2 ml) and acetic acid (1.5 ml) were added to2-(4-chlorophenoxymethyl)-N-hydroxyaminomethylene-α-methoxyiminophenylacetamide(0.36 g, 1 mmol), and the mixture was stirred at 120° C. for 4 hours.After completion of the reaction, ether (150 ml) was added, and themixture was washed with saturated aqueous sodium bicarbonate solution(100 ml) twice. The ether layer was dried over anhydrous magnesiumsulfate and concentrated under reduced pressure, and the residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) andrecrystallized from ethyl acetate/n-hexane to give2-(4-chlorophenoxymethyl)phenyl 1,2,4-oxadiazol-5-yl ketoneO-methyloxime (0.14 g, 40.8%) as colorless crystals.

mp. 96-97.5° C.

¹H-NMR(CDCl₃) δ ppm: 4.09(3H,s), 4.94(2H,s), 6.66-6.70(2H,m),7.14-7.17(2H,m), 7.28-7.60(4H,m), 8.44(1H,s).

Example 8 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl3-ethyl-1,2,4-oxadiazol-5-yl ketone O-methyloxime

Dichloroethane (5 ml), thionyl chloride (0.65 g, 5.5 mmol) anddimethylformamide (0.05 ml) were added to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetic acid (1.57 g, 5mmol), and the mixture was stirred under reflux for 2 hours. Aftercompletion of the reaction, the mixture was concentrated under reducedpressure, pyridine (3 ml) and 1-hydroxyimino-l-propylamine (0.88 g, 10mmol) were added to the residue, and the mixture was stirred underreflux for 0.5 hours. After completion of the reaction, ether (150 ml)was added, and the mixture was washed with 1N hydrochloric acid (150 ml)twice. The ether layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure, and the residue was purified bysilica gel chromatography (ethyl acetate/n-hexane) and recrystallizedfrom ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl3-ethyl-1,2,4-oxadiazol-5-yl ketone O-methyloxime (0.63 g, 34.5%) ascolorless crystals.

mp. 111.5-112.5° C.

¹H-NMR(CDCl₃) δ ppm: 1.30(3H,t,J=7.3), 2.09(3H,s), 2.25(3H,s),2.77(2H,q,J=7.3), 4.11(3H,s), 4.95(2H,s), 6.54(1H,s), 6.65(1H,d,J=7.9),6.98(1H,d,J=7.3), 7.27-7.66(4H,m).

Example 9 Synthesis of2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetohydrazide

Methanol (10 ml), THF (10 ml) and hydrazine monohydrate (1.68 g, 0.03mol) were added to methyl2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetate (3.27 g, 0.01mol), and the mixture was stirred at room temperature for 3 hours. Aftercompletion of the reaction, water (200 ml) was added, and the mixturewas extracted with dichloromethane. The dichloromethane layer was driedover anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was recrystallized from ethyl acetate/n-hexane togive 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetohydrazide(2.93 g, 89.6%) as colorless crystals.

mp. 124.5-126° C.

¹H-NMR(CDCl₃) δ ppm: 2.18(3H,s), 2.29(3H,s), 3.88 (2H,d,J=4.3),3.96(3H,s), 4.92(2H,s), 6.61(1H,s), 6.67 (1H,d,J=7.3), 7.01(1H,d,J=7.3),7.21-7.59(4H,m), 7.76(1H,brs).

Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-ylketone O-methyloxime

Ethyl orthoformate (2 ml) was added to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetohydrazide (0.49g, 1.5 mmol), and the mixture was stirred under reflux for 4 hours.After completion of the reaction, water (100 ml) was added, and themixture was extracted with dichloromethane. The dichloromethane layerwas dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The residue was recrystallized from ethylacetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl1,3,4-oxadiazol-2-yl ketone O-methyloxime (0.10 g, 19.8%) as colorlesscrystals.

mp. 134-135° C.

¹H-NMR(CDCl₃) δ ppm: 2.08(3H,s), 2.25(3H,s), 4.08(3H,s), 4.96(2H,s),6.54(1H,s), 6.65(1H,d,J=7.3), 6.97(1H,d,J=7.9), 7.32-7.64(4H,m),8.93(1H,s).

Example 10 Synthesis ofα-amino-2-(4-chlorophenoxymethyl)-α-hydroxyiminoacetophenoneO-methyloxime

28% sodium methoxide/methanol solution (1.31 g, 6.8 mmol) was added to amixture of hydroxylamine hydrochloride (0.47 g, 6.8 mmol) and methanol(10 ml) under ice-cooling over 5 minutes. Then,2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile (1.02 g, 3.4mmol) was added, and the mixture was stirred under reflux for 1.5 hours.After completion of the reaction, water (200 ml) was added, and themixture was extracted with dichloromethane. The dichloromethane layerwas dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The residue was recrystallized from ethylacetate/n-hexane to giveα-amino-2-(4-chlorophenoxymethyl)-α-hydroxyiminoacetophenoneO-methyloxime (0.87 g, 76.7%) as colorless crystals.

mp. 200° C. (decomposition)

¹H-NMR(CDCl₃) δ ppm: 3.92(3H,s), 4.93(2H,s), 5.04(2H,brs),6.79-6.87(2H,m), 7.15-7.21(3H,m), 7.33-7.52(3H,m).

Synthesis of 2-(4-chlorophenoxymethyl)phenyl 1,2,4-oxadiazol-3-yl ketoneO-methyloxime

Ethyl orthoformate (2 ml) was added toα-amino-2-(4-chlorophenoxymethyl)-α-hydroxyiminoacetophenoneO-methyloxime (0.40 g, 1.2 mmol), and the mixture was stirred underreflux for 4 hours. After completion of the reaction, toluene (10 ml)was added, and the mixture was concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give2-(4-chlorophenoxymethyl)phenyl 1,2,4-oxadiazol-3-yl ketoneO-methyloxime (0.36 g, 87.3%) as colorless crystals.

mp. 107-1080° C.

¹H-NMR(CDCl₃) δ ppm: 4.08(3H,s), 4.96(2H,s), 6.72-6.75(2H,m),7.14-7.18(2H,m), 7.28-7.60(4H,m), 8.76(1H,s).

Example 11 Synthesis of 2-(4-chlorophenoxymethyl)phenyl5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime

Acetic anhydride (2 ml) was addedα-amino-2-(4-chlorophenoxymethyl)-α-hydroxyiminoacetophenoneO-methyloxime (0.40 g, 1.2 mmol), and the mixture was stirred underreflux for 5 hours. After completion of the reaction, the reactionmixture was concentrated under reduced pressure, ether (100 ml) wasadded, and the mixture was washed with saturated aqueous sodiumbicarbonate solution (50 ml) twice. The ether layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give2-(4-chlorophenoxymethyl)phenyl 5-methyl-1,2,4-oxadiazol-3-yl ketoneO-methyloxime (0.35 g, 81.5%) as colorless crystals.

mp. 125-126° C.

¹H-NMR(CDCl₃) δ ppm: 2.65(3H,s), 4.07(3H,s), 4.96(2H,s),6.74-6.77(2H,m), 7.15-7.18(2H,m), 7.26-7.59(4H,m).

Example 12 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl1H-tetrazol-5-yl ketone O-methyloxime

Sodium azide (1.30 g, 20 mmol), ammonium chloride (1.07 g, 20 mmol) anddimethylformamide (10 ml) were added to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (0.59 g,2 mmol), and the mixture was stirred at 115° C. for 9 hours. Aftercompletion of the reaction, ethyl acetate (150 ml) was added, and themixture was washed with saturated brine (100 ml) twice. The ethylacetate layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was recrystallized fromethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl1H-tetrazol-5-yl ketone O-methyloxime (0.59 g, 87.4%) as colorlesscrystals.

mp. 168-170° C.

¹H-NMR(CDCl₃) δ ppm: 2.00(3H,s), 2.25(3H,s), 4.05(3H,s), 4.95(2H,s),6.52(1H,s), 6.65(1H,d,J=7.3), 6.96(1H,d,J=7.3), 7.32-7.63(4H,m).

Example 13 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl

1-methyl-1H-tetrazol-5-yl ketone O-methyloxime and2-(2,5-dimethylphenoxymethyl)phenyl 2-methyl-2H-tetrazol-5-yl ketoneO-methyloxime

Dimethylformamide (3 ml) and potassium carbonate (0.33 g, 2.4 mmol) wereadded to 2-(2,5-dimethylphenoxy methyl)phenyl 1H-tetrazol-5-yl ketoneO-methyloxime (0.40 g, 1.2 mmol), and the mixture was stirred at roomtemperature for 5 minutes. Then, dimethyl sulfate (0.23 g, 1.8 mmol) wasadded under ice-cooling, and the mixture was stirred at room temperatureovernight. After completion of the reaction, ether (150 ml) was added,and the mixture was washed with brine (50 ml) twice. The ether layer wasdried over anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give2-(2,5-dimethylphenoxymethyl)phenyl 1-methyl-1H-tetrazol-5-yl ketoneO-methyloxime as colorless crystals (0.16 g, 37.9%) [mp. 115.5-116.5°C.; ¹H-NMR(CDCl₃) δ ppm: 1.97(3H,s), 2.26(3H,s), 4.06(3H,s), 4.13(3H,s),4.89(2H,s), 6.50(1H,s), 6.65(1H,d,J=7.9), 6.97(1H,d,J=7.9),7.34-7.58(4H,m)] and 2-(2,5-dimethylphenoxymethyl)phenyl2-methyl-2H-tetrazol-5-yl ketone O-methyloxime as colorless crystals(0.08 g, 19.0%) [mp. 131-132° C.; ¹H-NMR(CDCl₃) δ ppm: 2.12(3H,s),2.24(3H,s), 4.09(3H,s), 4.34(3H,s), 4.96(2H,s), 6.54(1H,s),6.64(1H,d,J=7.9), 6.98(1H,d,J=7.3), 7.29-7.53(3H,m), 7.69(1H,d,J=7.3)].

Example 14 Synthesis of 2-(3-chlorophenoxymethyl)phenyl1-methyl-2-imidazolin-2-yl ketone O-methyloxime

Xylene (5 ml) and benzene (5 ml) were added to2-(3-chlorophenoxymethyl)-(α-methoxyiminophenylacetonitrile (1.0 g, 3.3mmol), N-methylethylenediamine (740 mg, 10 mmol) and zinc acetatedihydrate (100 mg, 0.46 mmol), and the mixture was subjected toazeotropic dehydration and stirred at 140° C. for 18 hours. Afterallowing the mixture to stand for cooling, ethyl acetate was added tothe reaction mixture. The mixture was washed successively with water andsaturated brine and dried over anhydrous sodium sulfate, and the solventwas evaporated under reduced pressure. The residue was purified bycolumn chromatography on activated alumina containing water (5%) (ethylacetate/n-hexane) and column chromatography on silica gel (ethylacetate/n-hexane) to give isomer A (720 mg, 60%, as an oil) and isomer B(220 mg, 19%, as an oil) of 2-(3-chlorophenoxymethyl)phenyl1-methyl-2-imidazolin-2-yl ketone O-methyloxime.

Isomer A: ¹H-NMR(CDCl₃) δ ppm: 2.75(3H,s), 3.41(2H,t,J=9.8),3.92(2H,t,J=9.8), 3.97(3H,s), 5.35(2H,s), 6.84(1H,ddd,J=8.0,2.4,0.9),6.93(1H,ddd,J=8.0,1.8,0.9), 6.99(1H,dd,J=2.4,1.8), 7.19(1H,t,J=8.0),7.32-7.44(2H,m), 7.51(1H,dd,J=7.3,1.4), 7.64(1H,d,J=7.0).

Isomer B: ¹H-NMR(CDCl₃) δ ppm: 3.03(3H,s), 3.38(2H,t,J=9.9),3.77(2H,t,J=9.9), 3.97(3H,s), 4.99(2H,s), 6.83(1H,dd,J=8.5,2.5),6.91(1H,d,J=7.8), 6.94(1H,brs), 7,16(1H,dd,J=8.3,7.8), 7.23(1H,d,J=7.6),7.34-7.39(2H,m), 7,49(1H,d,J=6.4).

Example 15 Synthesis of 2-(3-methylphenoxymethyl)phenyl 2-oxazolin-2-ylketone O-methyloxime

Ethylene glycol (2 ml) and benzene (10 ml) were added to2-(3-methylphenoxymethyl)-α-methoxyiminophenyl acetonitrile (1.0 g, 3.6mmol), 2-aminoethanol (400 mg, 6.6 mmol) and zinc acetate dihydrate (100mg, 0.46 mmol), and the mixture was subjected to azeotropic dehydrationand stirred at 100° C. for 20 hours. After allowing the mixture to standfor cooling, ethyl acetate was added to the reaction mixture. Themixture was washed successively with water and saturated brine and driedover anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The residue was purified by column chromatography onsilica gel (ethyl acetate/n-hexane) to give2-(3-methylphenoxymethyl)phenyl 2-oxazolin-2-yl ketone O-methyloxime(280 mg,24%) as an oil.

¹H-NMR(CDCl₃) δ ppm: 2.31(3H,s), 4.00(2H,t,J=9.8), 4.03(3H,s),4.32(2H,t,J=9.8), 5.21(2H,s), 6.72-6.78(3H,m), 7.14(1H,t,J=7.6),7.31-7.48(3H,m), 7.62(1H,d,J=7.6).

Example 16 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl2-thiazolin-2-yl ketone O-methyloxime

2-Aminoethanethiol hydrochloride (2.80 g, 24.6 mmol), zinc acetatedihydrate (600 mg, 2.7 mmol), toluene (12 ml) and triethylamine (3.12 g,30.8 mmol) were added to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (6.00 g,20.4 mmol), and the mixture was stirred under reflux for 14 hours. Aftercompletion of the reaction, water (100 ml) was added, and the mixturewas extracted with ethyl acetate. The ethyl acetate layer was dried overanhydrous sodium sulfate and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)phenyl2-thiazolin-2-yl ketone O-methyloxime (5.71 g, 79.0%) as crystals.

mp. 79-82° C.

¹H-NMR(CDCl₃) δ ppm: 2. 24(2. 23) (3H, s), 2.29(2 .28) (3H,s),3.21(3.27)(2H,t,J=8.6), 4.07(4.02)(3H,s), 4.24(3.36) (2H,t,J=8.6),5.11(4.93)(2H,s), 6.56-7.63(7H,m).

Example 17 Synthesis of2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde

1M diisobutylaluminum hydride/toluene solution (5.5 ml, 5.5 mmol) wasadded dropwise to a mixture of methyl2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetate (1.64 g, 5mmol) and dichloromethane (15 ml) at −70° C. over 0.5 hours, and thenthe mixture was stirred at −70° C. to room temperature for 3 hours.Methanol (3 ml) was added to the reaction mixture, and the mixture wasstirred at room temperature for 1 hour. The precipitated insolublematerials were removed, and the mixture was concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde (0.54 g,36.3%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 2.16(3H,s), 2.28(3H,s), 4.11(3H,s), 4.86(2H,s),6.55(1H,s), 6.67(1H,d,J=7.3), 6.99-7.58(5H,m), 9.69(1H,s).

Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl oxazol-5-yl ketoneO-methyloxime

p-Toluenesulfonylmethylisocyanide (0.23 g, 1.2 mmol), potassiumcarbonate (0.18 g, 1.3 mmol) and methanol (2 ml) were added to2-(2,5-dimethylphenoxymethyl)-α-methoxy-iminophenylacetaldehyde (0.30 g,1 mmol), and the mixture stirred under reflux for 2 hours. Aftercompletion of the reaction, ether (100 ml) was added, and the mixturewas washed with brine (80 ml) twice. The ether layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give2-(2,5-dimethylphenoxy-methyl)phenyl oxazol-5-yl ketone O-methyloxime(0.15 g, 44.6%) as colorless crystals.

mp. 90-91° C.

¹H-NMR(CDCl₃) δ ppm: 2.12(3H,s), 2.24(3H,s), 4.01(3H,s), 4.96(2H,s),6.54(1H,s), 6.65(1H,d,J=7.3), 6.88(1H,s), 6.98(1H,d,J=7.3),7.24-7.69(4H,m), 7.94(1H,s).

Example 18 Synthesis of 2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-ylketone O-methyloxime

Zinc acetate dihydrate (400 mg, 1.8 mmol), ethanolamine (975 mg, 15.9mmol) and xylene (8 ml) were added to2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile (4.00 g, 13.3mmol), and the mixture was stirred under reflux for 63 hours. Aftercompletion of the reaction, water (100 ml) was added, and the mixturewas extracted with ethyl acetate. The ethyl acetate layer was dried oversodium sulfate and concentrated under reduced pressure. The residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to giveisomer A (1.31 g, 28.6%, as crystals) and isomer B (0.45 g, 9.8%, ascrystals) of 2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-yl ketoneO-methyloxime.

Isomer A: mp. 97-100° C.

¹H-NMR(CDCl₃) δ ppm: 3.73(2H,t,J=7.9), 3.96 (2H,t,J=7.9), 4.07(3H,s),5.00(2H,s), 6.92-7.65(8H,m).

Isomer B: mp. 109-112° C.

¹H-NMR(CDCl₃) δ ppm: 3.92(2H,t,J=9.8), 4.02(3H,s), 4.39(2H,t,J=9.8),5.07(2H,s), 6.94-7.46(8H,m).

Synthesis of 2-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime

Anisole (152 ml) and aluminium chloride (16.3 g, 122 mmol) were added to2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime (19.08g, 55.3 mmol), and the mixture was stirred under ice-cooling for 1.5hours. After completion of the reaction, water (100 ml) was added, andthe mixture was extracted with ethyl acetate. The ethyl acetate layerwas dried over anhydrous sodium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) to give 2-hydroxyphenyl 2-oxazolin-2-yl ketoneO-methyloxime (6.82 g, 56%) as an oil.

¹H-NMR(CDCl₃) δ ppm: 4.07(3H,s), 4.15(2H,t,J=9.5), 4.50(2H,t,J=9.5),6.85-7.35(5H,m).

Synthesis of 2-(5-trifluoromethyl-2-pyridyloxy)phenyl 2-oxazolin-2-ylketone O-methyloxime

DMF (2.2 ml), potassium carbonate (210 mg, 1.5 mmol) and2-chloro-5-trifluoromethylpyridine (220 mg, 1.2 mmol) were added to2-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime (220 mg, 1.0 mmol),and the mixture was stirred at 100° C. for 2.5 hours. After completionof the reaction, 1N NaOH (100 ml) was added, and the mixture wasextracted with ether. The ether layer was dried over anhydrous sodiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to give2-(5-trifluoromethyl-2-pyridyloxy)phenyl 2-oxazolin-2-yl ketoneO-methyloxime (190 mg, 52.1%) as an oil.

¹H-NMR(CDCl₃) δ ppm: 3.78(2H,t,J=9.8), 3.98(3H,s), 4.16(2H,t,J=9.8),6.94-7.87(6H,m), 8.43(1H,brs).

Isomer A: mp. 97-100° C.

¹H-NMR(CDCl₃) δ ppm: 3.73(2H,t,J=7.9), 3.96 (2H,t,J=7.9), 4.07(3H,s),5.00(2H,s), 6.92-7.65(8H,m).

Isomer B: mp. 109-112° C.

¹H-NMR(CDCl₃) δ ppm: 3.92(2H,t,J=9.8), 4.02(3H,s), 4.39(2H,t,J=9.8),5.07(2H,s), 6.94-7.46(8H,m).

Synthesis of 2-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime

Anisole (152 ml) and aluminium chloride (16.3 g, 122 mmol) were added to2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime (19.08g, 55.3 mmol), and the mixture was stirred under ice-cooling for 1.5hours. After completion of the reaction, water (100 ml) was added, andthe mixture was extracted with ethyl acetate. The ethyl acetate layerwas dried over anhydrous sodium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) to give 2-hydroxyphenyl 2-oxazolin-2-yl ketoneO-methyloxime (6.82 g, 56.0%) as an oil.

¹H-NMR(CDCl₃) δ ppm: 4.07(3H,s), 4.15(2H,t,J=9.5), 4.50(2H,t,J=9.5),6.85-7.35(5H,m).

Synthesis of 2-(5-trifluoromethyl-2-pyridyloxy)phenyl 2-oxazolin-2-ylketone O-methyloxime

DMF (2.2 ml), potassium carbonate (210 mg, 1.5 mmol) and2-chloro-5-trifluoromethylpyridine (220 mg, 1.2 mmol) were added to2-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime (220 mg, 1.0 mmol),and the mixture was at 100° C. for 2.5 hours. After completion of thereaction, 1N NaOH (100 ml) was added, and the mixture was extracted withether. The ether layer was dried over anhydrous sodium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give2-(5-trifluoromethyl-2-pyridyloxy)phenyl 2-oxazolin-2-yl ketoneO-methyloxime (190 mg, 52.1%) as an oil.

¹H-NMR(CDCl₃) δ ppm: 3.78(2H,t,J=9.8), 3.98(3H,s), 4.16(2H,t,J=9.8),6.94-7.87(6H,m), 8.43(1H,brs).

Example 19 Synthesis of5-chloro-2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile

Dimethyl sulfoxide (3 ml) and 95% sodium cyanide (0.31 g, 6 mmol) wereadded to 5-chloro-2-(4-chlorobenzyloxy)-α-methoxyiminobenzyl chloride(1.03 g, 3 mmol), and the mixture was stirred at 100° C. for 4 hours.After completion of the reaction, ethyl acetate (150 ml) was added, andthe mixture was washed with saturated brine (100 ml) twice. The ethylacetate layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give5-chloro-2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile (0.92 g,91.5%) as crystals.

¹H-NMR(CDCl₃) δ ppm: 4.20(3H,s), 5.15(2H,s), 6.90-7.41(6H,m),7.52(1H,d,J=2.4).

Synthesis of 5-chloro-2-(4-chlorobenzyloxy)phenyl5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime

28% sodium methoxide/methanol solution (1.04 g, 5.4 mmol) was added to amixture of hydroxylamine hydrochloride (0.38 g, 5.4 mmol) and methanol(6 ml) under ice-cooling over 5 minutes. Then,5-chloro-2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile (0.91 g,2.7 mmol) was added, and the mixture was stirred under reflux for 1.5hours. After completion of the reaction, water (100 ml) was added, andthe mixture was extracted with dichloromethane. The dichloromethanelayer was dried over anhydrous magnesium sulfate and concentrated underreduced pressure to giveα-amino-5-chloro-2-(4-chlorobenzyloxy)-α-hydroxyiminoacetophenoneO-methyloxime as acrude product.

Acetic anhydride (2 ml) was added to the crude product, and the mixturewas stirred under reflux for 2 hours. After completion of the reaction,the mixture was concentrated under reduced pressure, ethyl acetate (100ml) was added, and the mixture was washed with saturated aqueous sodiumbicarbonate solution (80 ml) twice. The ethyl acetate layer was driedover anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give5-chloro-2-(4-chlorobenzyloxy)phenyl 5-methyl-1,2,4-oxadiazol-3-ylketone O-methyloxime (0.35 g, 33.0%) as colorless crystals.

mp. 127-128.5° C.

¹H-NMR(CDCl₃) δ ppm: 2.38(3H,s), 4.12(3H,s), 4.85(2H,s),6.84-7.61(7H,m).

Synthesis of 5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-ylketone O-methyloxime

Aluminium chloride (0.27 g, 2 mmol) was added to a mixture of5-chloro-2-(4-chlorobenzyloxy)phenyl 5-methyl-1,2,4-oxadiazol-3-ylketone O-methyloxime (0.39 g, 1 mmol) and anisole (3 ml) underice-cooling, and the mixture was stirred at the same temperature for 1hour. After completion of the reaction, aqueous sodium bicarbonatesolution (100 ml) was added, and the mixture was extracted with ethylacetate. The ethyl acetate layer was dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to give5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-yl ketoneO-methyloxime (0.22 g, 82.2%) as colorless crystals. A part of thecrystals was recrystallized from ether/n-hexane to give crystals (mp.92-93.5° C.)

¹H-NMR(CDCl₃) δ ppm: 2.75(3H,s), 4.06(3H,s), 6.82-7.27(3H,m),10.22(1H,s).

Synthesis of 5-chloro-2-(5-trifluoromethyl-2-pyridyloxy)phenyl5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime

Dimethylformamide (1 ml), potassium carbonate (0.10 g, 0.74 mmol) and5-trifluoromethyl-2-chloropyridine (0.10 g, 0.56 mmol) were added to5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-yl ketoneO-methyloxime (0.10 g, 0.37 mmol), and the mixture was stirred at 110°C. for 2 hours. After completion of the reaction, ether (100 ml) wasadded, and the mixture was washed with saturated brine (80 ml) twice.The ether layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give5-chloro-2-(5-trifluoromethyl-2-pyridyloxy)phenyl5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime (0.14 g, 91.7%) as acolorless oil.

¹H-NMR(CDCl₃) δ ppm: 2.46(3H,s), 4.03(3H,s), 6.77(1H,d,J=9.2),7.16(1H,d,J=9.2), 7.44-7.86(3H,m), 8.36(1H,d,J=1.8).

Example 20 Synthesis of2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile

Dimethyl sulfoxide (2 ml) and 95% sodium cyanide (0.21 g, 0.004 mol)were added to 2-(2,5-dimethylphenoxy-methyl)-α-methoxyiminobenzylchloride (0.60 g, 0.02 mol), and the mixture was stirred at 110° C. for2 hours. After completion of the reaction, ether (100 ml) was added, andthe mixture was washed with water twice, dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to give2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (0.45 g,76.4%) as colorless crystals.

¹H-NMR (CDCl₃) δ ppm: 2.24(s,3H), 2.30(s,3H), 4.13(s,3H), 5.26(s,2H),6.62-7.76(m,7H).

Example 21 Synthesis2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile

Trifluoroacetic anhydride (3.15 g, 15 mmol) was added to a mixture of2-(4-chlorophenoxymethyl)-α-methoxy-iminophenylacetamide (1.19 g, 6mmol) and pyridine (12 ml) under ice-cooling over 20 minutes, and themixture was stirred at room temperature for 2 hours. After completion ofthe reaction, ether (150 ml) was added, and the mixture was washed with1N hydrochloric acid (150 ml), water (100 ml) and saturated aqueoussodium bicarbonate solution (100 ml). The ether layer was dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) to give2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile (1.57 g,87.0%) as colorless crystals.

mp. 69-71° C.

¹H-NMR(CDCl₃) δ ppm: 4.02(3H,s), 4.99(2H,s), 6.86-6.89(2H,m),7.23-7.26(2H,m), 7.36-7.56(4H,m).

Example 22 Synthesis of α-methoxyimino-2-methylphenylacetonitrile

85% potassium hydroxide (4.0 g, 61 mmol) and 2-methylphenylacetonitrile(6.6 g, 50 mmol) were added to toluene (33 ml), and the mixture wasice-cooled. Methanol (6.6 ml) was added dropwise, and then butyl nitrite(7.0 ml, 60 mmol) was added dropwise while maintaining the temperatureof the mixture at 25 to 35° C. The resulting mixture was stirred underice-cooling for 3 hours. After allowing the mixture to stand at roomtemperature overnight, water was added to the reaction mixture, and theresulting potassium salt of α-hydroxyimino-2-methylphenylacetonitrilewas extracted. Water was added to the extract to a volume of 100 ml.Toluene (50 ml) and tetrabutylammonium bromide (800 mg, 2.5 mmol) wereadded, and dimethyl sulfate (5.7 ml, 60 mmol) was added underice-cooling in 4 divided portions. The mixture was stirred at roomtemperature for additional 30 minutes, and then the organic layer wasseparated, washed successively with aqueous 1N sodium hydroxide solutionand saturated brine and dried over anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The residue was purifiedby silica gel chromatography (ethyl acetate/n-hexane) to give twogeometrical isomers A (6.0 g, 69%, as an oil) and B (1.2 g, 14%, as anoil) of α-methoxyimino-2-methylphenylacetonitrile.

Isomer A: ¹H-NMR(CDCl₃) δ ppm: 2.51(3H,s), 4.20(3H,s), 7.25-7.36(3H,m),7.54(1H,d,J=7.9).

Isomer B: ¹H-NMR(CDCl₃) δ ppm: 2.31(3H,s), 4.06(3H,s), 7.25-7.39(4H,m).

Synthesis of 2-bromomethyl-α-methoxyiminophenyl-acetonitrile

Benzene (80 ml) was added to α-methoxyimino-2-methylphenylacetonitrile(isomer A)(4.0 g, 23 mmol) and N-bromosuccinimide (4.9 g, 28 mmol), andthe mixture was heated under reflux for 1 hour in the presence ofazobisiso-butyronitrile (190 mg, 1.2 mmol) as a radical initiator. Afterallowing the mixture to stand for cooling, n-hexane (100 ml) was added,and the mixture was allowed to stand overnight, and the resultinginsoluble materials were filtered off. The filtrate was concentrated todryness under reduced pressure and purified by column chromatography onsilica gel (ethyl acetate/n-hexane) to give2-bromomethyl-α-methoxyiminophenyl-acetonitrile (4.4 g, 76%) as an oil.

¹H-NMR(CDCl₃) δ ppm: 4.30(3H,s), 4.79(2H,s), 7.42-7.50(3H,m),7.66-7.69(1H,m).

Synthesis of 2-(3-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile

2-Bromomethyl-α-methoxyiminophenylacetonitrile (5.0 g, 20 mmol) and3-chlorophenol (3.0 g, 23 mmol) were dissolved in dimethylformamide (25ml), and the mixture was stirred at room temperature for 2 hours in thepresence of potassium carbonate (3.3 g, 24 mmol). After completion ofthe reaction, diethyl ether (ca. 100 ml) was added to the reactionmixture, and the mixture was washed successively with water andsaturated brine. The organic layer was dried over anhydrous sodiumsulfate and concentrated to dryness under reduced pressure. The residuewas purified by column chromatography on silica gel (ethylacetate/n-hexane) and crystallized from diethyl ether/n-hexane to give2-(3-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile (3.7 g, 62%)as colorless crystals.

mp. 62-63° C.

¹H-NMR(CDCl₃) δ ppm: 4.11(3H,s), 5.25(2H,s), 6.82(1H,d,J=8.3),6.95-6.97(2H,m), 7.21(1H,t,J=8.3), 7.45-7.53(2H,m), 7.67(1H,d,J=7.3),7.75(1H,dd,J=7.3,1.5).

Example 23 Synthesis of 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene

Pyridinium p-toluenesulfonate (0.30 g, 0.0012 mol) was added to asolution of 2-bromobenzylalcohol (25 g, 0.134 mol) in dichloromethane(100 ml), and the mixture was stirred at room temperature.3,4-Dihydro-2H-pyran (16.86 g, 0.20 mol) was added thereto. The mixturewas stirred at room temperature for 2 hours. Then, saturated aqueoussodium bicarbonate solution (200 ml) was added, and the mixture wasextracted with dichloromethane (200 ml). After drying over anhydrousmagnesium sulfate, the solvent was evaporated to give the desired1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (36.00 g, yield: 99.3%)as an oil.

¹H-NMR(CDCl₃) δ ppm: 1.45-1.80(6H,m), 3.45-3.55(1H,m), 3.80-3.90(1H,m),4.52(1H,d,J=15.0), 4.80(1H,m), 4.90(1H,d,J=15.0), 7.16(1H,t,J=7.3),7.31(1H,t,J=7.3), 7.51(1H,d,J=7.3), 7.54(1H,d,J=7.3).

Example 24 Synthesis of 2-(2-tetrahydropyranyloxymethyl)phenyl3-methylisoxazol-5-yl ketone

Magnesium (0.73 g, 0.03 mol) and bromoethane (0.2 ml) were added to amixture of 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (5.42 g, 0.02mol) and THF (50 ml) under an atmosphere of nitrogen gas, and theresulting mixture was stirred at 50 to 60° C. for 1 hour to prepareGrignard reagent. The Grignard reagent was added dropwise to a mixtureof N-methoxy-3, N-dimethyl-5-isoxazolcarboxamide (3.40 g, 0.02 mol) andTHF (40 ml). The mixture was stirred at −60° C. to room temperature for1 hour, water (200 ml) was added, and the mixture was extracted withether (200 ml). The extract was dried over anhydrous magnesium sulfateand concentrated under reduced pressure. The residue was purified bysilica gel chromatography (ethyl acetate/n-hexane) to give2-(2-tetrahydropyranyloxymethyl)phenyl 3-methylisoxazol-5-yl ketone(4.09 g, yield: 67.9%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppM: 1.41-1.74(6H,m), 2.39(3H,s), 3.45-3.51(1H,m),3.75-3.83(1H,m), 4.59-4.60(1H,m), 4.71(1H,d,J=12.8), 4.94(1H,d,J=12.8),6.69(1H,s), 7.38-7.63(4H,m).

Example 25 Synthesis of 2-hydroxymethylphenyl 3-methylisoxazol-5-ylketone O-methyloxime

Methanol (25 ml), methoxyamine hydrochloride (2.17 g, 0.026 mol) andpyridine (2.1 ml, 0.026 mol) were added to2-(2-tetrahydropyranyloxymethyl)phenyl 3-methylisoxazol-5-yl ketone(4.09 g, 0.013 mol), and the mixture was stirred under reflux for 3hours. After completion of the reaction, half-saturated brine (200 ml)was added, and the mixture was extracted with dichloromethane (100 ml)twice. The extracts were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give isomer A (0.63 g,yield: 19.7%, as a colorless oil) and isomer B (1.62 g, yield: 50.7%, asa colorless oil) of 2-hydroxymethylphenyl 3-methylisoxazol-5-yl ketoneO-methyloxime.

Isomer A: ¹H-NMR(CDCl₃) δ ppm: 2.39(3H,s), 2.74(1H,t,J=6.7), 4.17(3H,s),4.54(2H,d,J=6.7), 7.02(1H,s), 7.33-7.55(4H,m).

Isomer B: ¹H-NMR(CDCl₃) δ ppm: 1.89(1H,t,J=6.1), 2.28(3H,s), 4.03(3H,s),4.52(2H,d,J=6.1), 6.05(1H,s), 7.17-7.62(4H,m).

Example 26 Synthesis of2-(3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)phenyl3-methylisoxazol-5-yl ketone O-methyloxime

THF (7.5 ml), 2,3-dichloro-5-trifluoromethylpyridine (0.81 g, 3.75 mmol)and 60% sodium hydride (0.12 g, 3.0 mmol) were added to2-hydroxymethylphenyl 3-methylisoxazol-5-yl ketone O-methyloxime (0.62g, 2.5 mmol) under ice-cooling, and the mixture was stirred at roomtemperature overnight. Water (100 ml) was added to the reaction mixture,and the mixture was extracted with ether (150 ml). The extract was driedover anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) to give isomer A (0.29 g, yield: 27.2%) and isomer B(0.76 g, yield: 71.4%) of2-(3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)phenyl3-methylisoxazol-5-yl ketone O-methyloxime.

Isomer A: mp. 77-79° C., ¹H-NMR(CDCl₃) δ ppm: 2.37(3H,s), 4.14(3H,s),5.45(2H,s), 6.97(1H,s), 7.36-7.63(4H,m), 7.79(1H,d,J=2.4),8.09(1H,d,J=2.4).

Isomer B: ¹H-NMR(CDCl₃) δ ppm: 2.28(3H,s), 4.04(3H,s), 5.33(2H,s),6.01(1H,s), 7.20-7.65(4H,m), 7.80(1H,d,J=2.2), 8.08(1H,d,J=2.2).

Example 27 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenylthiazolidin-2-yl ketone O-methyloxime

Toluene (3 ml), butanol (3 ml), cysteamine hydrochloride (0.34 g, 3.0mmol) and triethylamine (0.42 ml, 3 mmol) were added to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetoaldehyde (0.45 g,1.5 mmol), and the mixture was stirred at room temperature for 1 hour.After completion of the reaction, half-saturated brine (100 ml) wasadded, and the mixture was extracted with dichloromethane (50 ml) twice.The extracts were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give2-(2,5-dimethylphenoxymethyl)phenyl thiazolidin-2-yl ketoneO-methyloxime (0.49 g, yield 91.6%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 2.28(6H,s), 2.40(1H,brs), 2.81-3.06(3H,m),3.38-3.55(1H,m), 3.87(3H,s), 4.85-5.50(3H,m), 6.67-7.64(7H,m)

Example 28 Synthesis of 2-(2,5-dimethylphenoxymethyl)phenyl1,3-dioxolan-2-yl ketone O-methyloxime

Benzene (4 ml), ethylene glycol (0.12 g, 2.0 mmol) and p-toluenesulfonicacid monohydrate (0.01 g, 0.05 mmol) were added to2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde (0.3 g,1.0 mmol), and the mixture was subjected to azeotropic dehydration for 2hours. After completion of the reaction, half-saturated brine (100 ml)was added, and the mixture was extracted with dichloromethane (50 ml)twice. The extracts were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give2-(2,5-dimethylphenoxymethyl)phenyl 1,3-dioxolan-2-yl ketoneO-methyloxime (0.30 g, yield 87.9%) as colorless crystals. mp 136-137°C.

¹H-NMR(CDCl₃) δ ppm: 2.28(3H,m), 2.29(3H, s), 3.59-3.85(4H,m),3.92(3H,s), 5.04(1H,s), 5.09(1H,s), 5.63(1H,s), 6.66-7.62(7H,m).

Example 29 Synthesis of 1-bromo-2-(1-ethoxyethyl)oxymethylbenzene

Pyridinium p-toluenesulfonate (0.50 g, 0.002 mol) was added to a mixtureof 2-bromobenzylalcohol (18.70 g, 0.1 mol), dichloromethane (150 ml) andethyl vinyl ether (14.42 g, 0.2 mol) under ice-cooling, and the mixturewas stirred at room temperature for 3 hours. After completion of thereaction, half-saturated aqueous sodium bicarbonate solution (300 ml)was added, and the mixture was extracted with dichloromethane (100 ml)twice. The extracts were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure to give1-bromo-2-(1-ethoxyethyl)oxymethylbenzene (25.44 g, yield: 98.2%) as acolorless oil.

¹H-NMR(CDCl₃) δ ppm: 1.22(3H,t,J=7.3), 1.41(3H,t,J=5.5),3.49-3.77(2H,m), 4.59(1H,d,J=12.8), 4.70(1H,d,J=12.8), 4.87(1H,q,J=5.5),7.11-7.55(4H,m).

Example 30 Synthesis of 2-(1-ethoxyethyl)oxymethylphenyl5-methylisoxazol-3-yl ketone

A mixture of 1-bromo-2-(1-ethoxyethyl)oxymethylbenzene (12.96 g, 0.05mol) and THF (45 ml) was added to a mixture of magnesium (1.82 g, 0.075mol) and bromoethane (0.2 ml) and THF (5 ml) at 45 to 55° C. under anatmosphere of nitrogen gas, and the resulting mixture was stirred at 50to 55° C. for 1 hour to prepare a Grignard reagent. The Grignard reagentwas added dropwise to a mixture of N-methoxy-5,N-dimethyl-3-isoxazolcarboxamide (5.62 g, 0.033 mol) and THF (40 ml)cooled to −50° C. The mixture was stirred at −60° C. to room temperaturefor 1 hour, water (200 ml) was added, and the mixture was extracted withether (200 ml). The extract was dried over anhydrous magnesium sulfateand concentrated under reduced pressure. The residue was purified bysilica gel chromatography (ethyl acetate/n-hexane) to give2-(1-ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-yl ketone (8.61 g,yield: 90.2%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 1.16(3H,t,J=6.7), 1.27(3H,d,J=5.5), 2.52(3H,s),3.43-3.65(2H,m), 4.68-4.92(3H,m), 6.50(1H,s), 7.36-7.84(4H,m).

Example 31 Synthesis of 2-(1-ethoxyethyl)oxymethylphenyl5-methylisoxazol-3-yl ketone O-methyloxime

2-(1-Ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-yl ketone (4.34 g,0.015 mol) was added to a mixture of methanol (30 ml), methoxyaminehydrochloride (2.51 g, 0.03 mol) and 28% sodium methylate/methanolsolution (7.23 g, 0.0375 mol), and the mixture was stirred under refluxfor 3 hours. After completion of the reaction, half-saturated brine (200ml) was added, and the mixture was extracted with dichloromethane (100ml) twice. The extracts were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give2-(1-ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-yl ketoneO-methyloxime (4.32 g, yield: 90.5%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 1.11-1.26(6H,m), 2.47(2.43) (3H,s),3.39-3.60(2H,m), 4.08(3.97)(3H,s), 4.11-4.70(3H,m), 6.61(6.37)(1H,s),7.19-7.56(4H,m).

Example 32 Synthesis of 2-hydroxymethylphenyl 5-methylisoxazol-3-ylketone O-methyloxime

Methanol (26 ml) and pyridinium p-toluene-sulfonate (0.33 g, 0.0013 mol)were added to 2-(1-ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-ylketone O-methyloxime (4.14 g, 0.013 mol), and the mixture was stirredunder reflux for 0.5 hour. After completion of the reaction,half-saturated brine (300 ml) was added, and the mixture was extractedwith dichloromethane (100 ml) twice. The extracts were dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethylacetate/n-hexane) to give 2-hydroxymethylphenyl 5-methylisoxazol-3-ylketone O-methyloxime (2.95 g, yield: 92.1%) as a colorless oil.

¹H-NMR(CDCl₃) δ ppm: 2.43(3.18)(1H,t,J=6.7), 2.44(2.50)(3H,s),3.99(4.11)(3H,s), 4.47(4.57)(2H,d,J=6.7), 6.44(6.62)(1H,s),7.19-7.60(4H,m).

Example 33 Synthesis of2-(5-chloro-3-trifluoromethyl-2-pyridyloxymethyl)phenyl5-methylisoxazol-3-yl ketone O-methyloxime

THF (3 ml), 2,5-dichloro-3-trifluoromethylpyridine (0.32 g, 1.5 mmol)and 60% sodium hydride (0.05 g, 1.2 mmol) were added to2-hydroxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime (0.25g, 1.0 mmol) under ice-cooling, and the mixture was stirred at roomtemperature overnight. Water (100 ml) was added to the reaction mixture,and the mixture was extracted with ether (150 ml). The extract was driedover anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was purified by silica gel chromatography (ethylacetate/n-hexane) to give2-(5-chloro-3-trifluoromethyl-2-pyridyloxymethyl)phenyl5-methylisoxazol-3-yl ketone O-methyloxime (0.41 g, yield: 96.3%) ascolorless crystals.

mp. 120-121° C. (ether/n-hexane)

¹H-NMR (CDCl₃) δ ppm: 2.45(3H, s), 3.99 (3H, s), 5.34(2H,s), 6.39(1H,s),7.23-7.64(2H,m), 7.79(1H,d,J=2.5), 8.06(1H,d,J=2.5).

Example 34 Synthesis of 2-chloromethylphenyl 3-methylisoxazol-5-ylketone O-methyloxime

Benzene (5 ml) and thionyl chloride (0.36 g, 3.0 mmol) were added to2-hydroxymethylphenyl 3-methylisoxazol-5-yl ketone O-methyloxime (0.62g, 2.5 mmol), and the mixture was stirred at room temperature for 2hours. After completion of the reaction, the solvent was evaporatedunder reduced pressure. The residue was purified by silica gelchromatography (ethyl acetate/n-hexane) to give 2-chloromethylphenyl3-methylisoxazol-5-yl ketone O-methyloxime (0.26 g, yield: 39.3%) as acolorless oil.

¹H-NMR(CDCl₃) δ ppm: 2.29(3H,s), 4.04(3H,s), 4.47(2H,s), 6.05(1H,s),7.18-7.60(4H,m).

Example 35 Synthesis of2-(3,4-dichloro-α-methylbenzylideneaminooxymethyl)phenyl3-methylisoxazol-5-yl ketone O-methyloxime

DMF (3 ml), 3,4-dichloroacetophenone oxime (0.31 g, 1.5 mmol) andpotassium carbonate (0.28 g, 2.0 mmol) were added to2-chloromethylphenyl 3-methylisoxazol-5-yl ketone O-methyloxime (0.26 g,1.0 mmol), and the mixture was stirred at 60° C. for 2 hours. Water (100ml) was added to the reaction mixture, and the mixture was extractedwith ether (150 ml). The extract was dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel chromatography (ethyl acetate/n-hexane) to give2-(3,4-dichloro-α-methylbenzylideneaminooxymethyl)phenyl3-methylisoxazol-5-yl ketone O-methyloxime (0.37 g, yield: 85.6%) ascolorless crystals.

¹H-NMR(CDCl₃) δ ppm: 2.01(3H,s), 2.21(3H,s), 4.04(3H,s), 5.13(2H,s),5.96(1H,s), 7.20-7.64(7H,m). mp. 84-85° C.

Example 36 Synthesis of2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxy]-α-methoxyiminophenylacetaldehyde

1M diisobutylaluminum hydride/toluene solution (11 ml, 16.5 mmol) wasadded dropwise to a mixture of methyl2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxy]-α-methoxyiminophenylacetate(4.83 g, 11.8 mmol) and dichloromethane (47 ml) at −65° C. or lower over4 minutes, and the mixture was stirred at −78° C. to room temperaturefor 3 hours. Methanol (7 ml) was added to the reaction mixture, and themixture was stirred at room temperature for 1 hour. The precipitatedinsoluble materials were removed, and the remaining mixture wasconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxy]-α-methoxyiminophenylacetaldehyde(2.11 g, 47.3%) as a colorless

¹H-NMR(CDCl₃) δ ppm: 2.19(3H,s), 4.11(3H,s), 5.09(2H,s),7.09-7.12(1H,m), 7.36-7.52(4H,m), 7.59(1H,d,J=7.9), 7.77(1H,d,J=7.9),7.85(1H,s), 9.70(1H,s).

Example 37 Synthesis of 2-[(α-methyl-3-trifluoromethyl-benzylidene)aminooxy]phenyl thiazolidin-2-yl ketone O-methyloxime

Toluene (2.5 ml), butanol (2.5 ml), cysteamine hydrochloride (0.29 g,2.54 mmol) and triethylamine (0.26 g, 2.54 mmol) were added to2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxy]-α-methoxyiminophenylacetaldehyde(0.48 g, 1.27 mmol), and the mixture was stirred at room temperature for1 hour. After completion of the reaction, half-saturated brine (100 ml)was added, and the mixture was extracted with dichloromethane (50 ml)twice. The extracts were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was purified by silicagel chromatography (ethyl acetate/n-hexane) to give2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxy]phenylthiazolidin-2-yl ketone O-methyloxime (0.52 g, yield 93.6%) as acolorless oil.

¹H-NMR(CDCl₃) δ ppm: 2.39(3H,s), 2.75-3.10(3H,m), 3.50(2H,m),3.86(3H,s), 5.20-5.30(2H,m), 5.45(1H,m), 7.37-7.61(6H,m),7.82(1H,d,J=7.9), 7.91(1H,s).

According to the same manner as that in Examples 24 and 30, variouscompounds of the formula (XLVIII), which are intermediates forproduction of the compound (I), were synthesized. The compounds thusobtained and their physical data are as follows. In the followingtables, the physical data of the compounds (XLVIII-7) and (XLVIII-4)obtained in Examples 24 and 30, respectively, are also listed.

No R³ R⁴ P Physical data XLVIII-1 Isoxazol-3-yl H TetrahydropyranylXLVIII-2 Isoxazol-3-yl H 1-C₂H₅OC₂H₄ ¹H—NMR(CDCl₃) δ ppm :1.16(3H, t, J=7.3), 1.26(3H, d, J=5.5), 3.40- 3.65(2H, m), 4.70-4.93(3H, m), 6.89(1H,d, J=1.8), 7.37-7.87(4H, m), 8.53(1H, J=1.8) XLVIII-3 5-Me- HTetrahydropyranyl isoxazol-3-yl XLVIII-4 5-Me- H 1-C₂H₅OC₂H₄¹H—NMR(CDCl₃) δ ppm :1.16(3H, t, isoxazol-3-yl J=6.7), 1.27(3H, d,J=5.5), 2.52(3H, s), 3.43-3.65(2H, m), 4.68-4.92(3H, m), 6.50(1H, s),7.36-7.84(4H, m). XLVIII-5 Isoxazol-5-yl H Tetrahydropyranyl XLVIII-6Isoxazol-5-yl H 1-C₂H₅OC₂H₄ XLVIII-7 3-Me- H Tetrahydropyranyl¹H—NMR(CDCl₃) δ ppm :1.41-1.74 isoxaxol-5-yl (6H, m), 2.39(3H, s),3.45-3.51 (1H, m), 3.75-3.83 (1H, m), 4.59-4.60 (1H, m), 4.71 (1H, d,J=12.8), 4.94 (1H, d, J=12.8), 6.69(1H, s), 7.38- 7.63(4H, m). XLVIII-83-Me- H 1-C₂H₅OC₂H4 ¹H—NMR(CDCl₃) δ ppm :1.16(3H, t, isoxazol-5-ylJ=7.3), 1.25(3H, d, J=5.5), 2.40(3H, s), 3.42-3.61 (2H, m),4.68-4.88(3H, m), 6.70(1H, s), 7.37-7.66(4H, m) XLVIII-9 1,3,4- HTetrahydropyranyl Oxadiazol-2-yl XLVIII-10 1,3,4- H 1-C₂H₅OC₂H₄Oxadiazol-2-yl XLVIII-11 1-Me-imidazol- H Tetrahydropyranyl 2-ylXLVIII-12 1-Me-imidazol- H 1-C₂H₅OC₂H₄ 2-yl XLVIII-13 2-Isoxazolin-3- HTetrahydropyranyl yl XLVIII-14 2-Isoxazolin-3- H 1-C₂H₅OC₂H₄ ylXLVIII-15 5-Me-2- H Tetrahydropyranyl isoxazoIin-3-yl XLVIII-16 5-Me-2-H 1-C₂H₅OC₂H₄ isoxazolin-3-yl XLVIII-17 2-Furyl H TetrahydropyranylXLVIII-18 2-FuryI H 1-C₂H₅OC₂H₄ XLVIII-19 5-Me-1,2,4- HTretrhydropyranyl oxadiazol-3-yl XLVIII-20 5-Me-1,2,4- H 1-C₂H₅OC₂H₄oxadiazol-3-yl

According to the same manner as that in Examples described above,various compounds of the formula (I) were synthesized. The compoundsthus obtained and their physical data are as follows. In the followingtables, the physical data of the compounds obtained in the aboveExamples are also listed. “No.” represents a compound number. When theproduct is obtained as a mixture of isomers A/B, the δ values of eitherisomer are indicated in the parentheses.

The basic structures of the compound (I) in the tables are as follows:

No R¹ R² R³ n Physical data 1 C₆H₅ Me Imidazol-1-yl 1 mp 66-67.5° C. 22-F—C₆H₄ Me Imidazol-1-yl 1 3 3-F—C₆H₄ Me Imidazol-1-yl 1 4 4-F—C₆H₄ MeImidazol-1-yl 1 5 2-Cl—C₆H₄ Me Imidazol-1-yl 1 mp 79.5-80.5° C. 63-Cl—C₆H₄ Me Imidazol-1-yl 1 mp 96.5-97.5° C. 7 4-Cl—C₆H₄ MeImidazol-1-yl 1 mp 88-88.5° C. 8 2-Br—C₆H₄ Me Imidazol-1-yl 1 93-Br—C₆H₄ Me Imidazol-1-yl 1 10 4-Br—C₆H₄ Me Imidazol-1-yl 1 11 3-I—C₆H₄Me Imidazol-1-yl 1 12 4-I—C₆H₄ Me Imidazol-1-yl 1 13 2-Me—C₆H₄ MeImidazol-1-yl 1 ¹H-NMR(CDCl₃)δppm: 2.15(3H, s), 3.99(3H, s), 4.98(2H,s), 6.68-7.66(10H, m), 7.96(1H, s) 14 3-Me—C₆H₄ Me Imidazol-1-yl 1 154-Me—C₆H₄ Me Imidazol-1-yl 1 mp 58-65° C. 16 2-Et—C₆H₄ Me Imidazol-2-yl1 ¹H-NMR(CDCl₃)δppm: 1.16(3H, t, J=7.3), 2.60(2H, q, J=7.3), 3.99(3H,s), 4.98(2H, s), 6.69-7.67(10H, m), 7.96(1H, s) 17 3-Et—C₆H₄ MeImidazol-1-yl 1 18 4-Et—C₆H₄ Me Imidazol-1-yl 1 19 2-MeO—C₆H₄ MeImidazol-1-yl 1 20 3-MeO—C₆H₄ Me Imidazol-1-yl 1 21 4-MeO—C₆H₄ MeImidazol-1-yl 1 22 2-CF₃—C₆H₄ Me Imidazol-1-yl 1 23 3-CF₃—C₆H₄ MeImidazol-1-yl 1 24 4-CF₃—C₆H₄ Me Imidazol-1-yl 1 25 2,3-F₂—C₆H₃ MeImidazol-1-yl 1 26 2,4-F₂—C₆H₃ Me Imidazol-1-yl 1 27 2,5-F₂—C₆H₃ MeImidazol-1-yl 1 28 2,6-F₂—C₆H₃ Me Imidazol-1-yl 1 29 3,4-F₂—C₆H₃ MeImidazol-1-yl 1 30 3,5-F₂—C₆H₃ Me Imidazol-1-yl 1 31 2,3-Cl₂—C₆H₃ MeImidazol-1-yl 1 32 2,4-Cl₂—C₆H₃ Me Imidazol-1-yl 1 33 2,5-Cl₂—C₆H₃ MeImidazol-1-yl 1 34 2,6-Cl₂—C₆H₃ Me Imidazol-1-yl 1 35 3,4-Cl₂—C₆H₃ MeImidazol-1-yl 1 36 3,5-Cl₂—C₆H₃ Me Imidazol-1-yl 1 37 2,3-Me₂—C₆H₃ MeImidazol-1-yl 1 38 2,4-Me₂—C₆H₃ Me Imidazol-1-yl 1 39 2,5-Me₂—C₆H₃ MeImidazol-1-yl 1 ¹H-NMR(CDCl₃)δppm: 2.11(3H, s), 2.26(3H, s), 3.99(3H,s), 4.96(2H, s), 6.52(1H, s), 6.66(1H, d, J=7.3), 6.98-7.66(7H, m),7.96(1H, s) 40 2,6-Me₂—C₆H₃ Me Imidazol-1-yl 1 ¹H-NMR(CDCl₃)δppm:2.17(6H, s), 4.01(3H, s), 4.78(2H, s), 6.89-7.85(9H, m), 8.04(1H, s) 413,4-Me₂—C₆H₃ Me Imidazol-1-yl 1 42 3,5-Me₂—C₆H₃ Me Imidazol-1-yl 1 432-Cl-4-Me—C₆H₃ Me Imidazol-1-yl 1 44 2-Cl-5-Me—C₆H₃ Me Imidazol-1-yl 145 2-Cl-3-Me—C₆H₃ Me Imidazol-1-yl 1 46 4-Cl-3-Me—C₆H₃ Me Imidazol-1-yl1 47 2,3,5-Me₂—C₆H₃ Me Imidazol-1-yl 1 48 3-Ph—C₆H₄ Me Imidazol-1-yl 149 4-Ph—C₆H₄ Me Imidazol-1-yl 1 50 2-i-Pr—C₆H₄ Me Imidazol-1-yl 1 513-i-Pr—C₆H₄ Me Imidazol-1-yl 1 52 4-i-Pr—C₆H₄ Me Imidazol-1-yl 1 533-t-Bu—C₆H₄ Me Imidazol-1-yl 1 54 4-t-Bu—C₆H₄ Me Imidazol-1-yl 1 553-i-PrO—C₆H₄ Me Imidazol-1-yl 1 56 4-i-PrO—C₆H₄ Me Imidazol-1-yl 1 572-Cl-pyridin-3-yl Me Imidazol-1-yl 1 mp 107.5-108.5° C. 58 4-MeS—C₆H₄ MeImidazol-1-yl 1 59 Pyridin-3-yl Me Imidazol-1-yl 1 60 2,4,5-Cl₃—C₆H₂ MeImidazol-1-yl 1 61 C₆H₅ Et Imidazol-1-yl 1 ¹H-NMR(CDCl₃)δppm: 1.30(3H,t, J=6.7), 4.21(2H, q, J=6.7), 5.02(2H, s), 6.78- 7.64(11H, m), 8.04(1H,s) 62 2-F—C₆H₄ Et Imidazol-1-yl 1 63 3-F—C₆H₄ Et Imidazol-1-yl 1 644-F—C₆H₄ Et Imidazol-1-yl 1 65 2-Cl—C₆H₄ Et Imidazol-1-yl 1 66 3-Cl—C₆H₄Et Imidazol-1-yl 1 67 4-Cl—C₆H₄ Et Imidazol-1-yl 1 68 2-Br—C₆H₄ EtImidazol-1-yl 1 69 3-Br—C₆H₄ Et Imidazol-1-yl 1 70 4-Br—C₆H₄ EtImidazol-1-yl 1 71 3-I—C₆H₄ Et Imidazol-1-yl 1 72 2-Me—C₆H₄ EtImidazol-1-yl 1 73 3-Me—C₆H₄ Et Imidazol-1-yl 1 74 4-Me—C₆H₄ EtImidazol-1-yl 1 75 2-Et—C₆H₄ Et Imidazol-1-yl 1 76 3-Et—C₆H₄ EtImidazol-1-yl 1 77 4-Et—C₆H₄ Et Imidazol-1-yl 1 78 2-MeO—C₆H₄ EtImidazol-1-yl 1 79 3-MeO—C₆H₄ Et Imidazol-1-yl 1 80 4-MeO—C₆H₄ EtImidazol-1-yl 1 81 C₆H₅ Allyl Imidazol-1-yl 1 ¹H-NMR(CDCl₃)δppm: 4.63-4.66(2H, m), 5.02(2H, s), 5.20- 5.33(2H, m), 5.86-6.01(1H, m),6.77-7.64(11H, m), 8.03(1H, s) 82 2-F—C₆H₄ Allyl Imidazol-1-yl 1 833-F—C₆H₄ Allyl Imidazol-1-yl 1 84 4-F—C₆H₄ Allyl Imidazol-1-yl 1 852-Cl—C₆H₄ Allyl Imidazol-1-yl 1 86 2-Cl—C₆H₄ Allyl Imidazol-1-yl 1 874-Cl—C₆H₄ Allyl Imidazol-1-yl 1 88 2-Br—C₆H₄ Allyl Imidazol-1-yl 1 893-Br—C₆H₄ Allyl Imidazol-1-yl 1 90 4-Br—C₆H₄ Allyl Imidazol-1-yl 1 913-I—C₆H₄ Allyl Imidazol-1-yl 1 92 2-Me—C₆H₄ Allyl Imidazol-1-yl 1 933-Me—C₆H₄ Allyl Imidazol-1-yl 1 94 4-Me—C₆H₄ Allyl Imidazol-1-yl 1 952-Et—C₆H₄ Allyl Imidazol-1-yl 1 96 3-Et—C₆H₄ Allyl Imidazol-1-yl 1 974-Et—C₆H₄ Allyl Imidazol-1-yl 1 98 2-MeO—C₆H₄ Allyl Imidazol-1-yl 1 992-MeO—C₆H₄ Allyl Imidazol-1-yl 1 100 4-MeO—C₆H₄ Allyl Imidazol-1-yl 1101 C₆H₅ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₃)δ imidazol-2-yl ppm: 3.85(3H,s), 3.95(3H, s), 4.93(2H, s), 6.80-7.57(11H, m) Isomer B: ¹H-NMR(CDCl₃)δppm: 3.51(3H, s), 3.99(3H, s), 4.91(2H, s), 6.83-7.57(11H, m) 1022-F—C₆H₄ Me 1-Me- 1 imidazol-2-yl 103 3-F—C₆H₄ Me 1-Me- 1 imidazol-2-yl104 4-F—C₆H₄ Me 1-Me- 1 Isomer A: mp 99.5-100.5° C. imidazol-2-yl IsomerB: mp 114.5-115.5° C. 105 2-Cl—C₆H₄ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₃)δimidazol-2-yl ppm: 3.91(3H, s), 3.96(3H, s), 5.04(2H, s), 6.81-7.65(10H,m) Isomer B: mp 146.5-147.5° C. 106 3-Cl—C₆H₄ Me 1-Me- 1 Isomer A:¹H-NMR(CDCl₃)δ imidazol-2-yl ppm: 3.88(3H, s), 3.96(3H, s), 4.94(2H, s),6.69-7.54(10H, m) Isomer B: ¹H-NMR(CDCl₃)δ ppm: 3.53(3H, s), 4.00(3H,s), 4.94(2H, s), 6.74-7.55(10H, m) 107 4-Cl—C₆H₄ Me 1-Me- 1 Isomer A: mp122.0-123.0° C. imidazol-2-yl Isomer B: mp 144.5-145.5° C. 108 2-Br—C₆H₄Me 1-Me- 1 imidazol-2-yl 109 3-Br—C₆H₄ Me 1-Me- 1 imidazol-2-yl 1104-Br—C₆H₄ Me 1-Me- 1 imidazol-2-yl 111 3-I—C₆H₄ Me 1-Me- 1 imidazol-2-yl112 2-Me—C₆H₄ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₃)δ imidazol-2-yl ppm:2.18(3H, s), 3.85(3H, s), 3.96(3H, s), 4.93(2H, s), 6.73- 7.60(10H, m)Isomer B: mp 126.0-127.0° C. 113 3-Me—C₆H₄ Me 1-Me- 1 Isomer A: mp88.0-91.0° C. imidazol-2-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.31(3H, s),3.51(3H, s), 4.01(3H, s), 4.89(2H, s), 6.63- 7.65(10H, m) 114 4-Me—C₆H₄Me 1-Me- 1 Isomer A: mp 105.5-106.5° C. imidazol-2-yl Isomer B: mp118.5-119.5° C. 115 2-Et—C₆H₄ Me 1-Me- 1 imidazol-2-yl 116 3-Et—C₆H₄ Me1-Me- 1 imidazol-2-yl 117 4-Et—C₆H₄ Me 1-Me- 1 imidazol-2-yl 1182-MeO—C₆H₄ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₃)δ imidazol-2-yl ppm:3.85(3H, s), 3.91(3H, s), 3.96(3H, s), 5.04(2H, s), 6.74-7.65(10H, m)Isomer B: mp 108.5-109.5° C. 119 2-MeO—C₆H₄ Me 1-Me- 1 Isomer A:¹H-NMR(CDCl₃)δ imidazol-2-yl ppm: 3.74(3H, s), 3.85(3H, s), 3.95(3H, s),4.91(2H, s), 6.38-7.56(10H, m) Isomer B: ¹H-NMR(CDCl₃)δ ppm: 3.52(3H,s), 3.77(3H, s), 4.00(3H, s), 4.89(2H, s), 6.44- 7.56(10H, m) 1204-MeO—C₆H₄ Me 1-Me- 1 imidazol-2-yl 121 2-CF₃—C₆H₄ Me 1-Me- 1imidazol-2-yl 122 3-CF₃—C₆H₄ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₃)δimidazol-2-yl ppm: 3.86(3H, s), 3.95(3H, s), 4.99(2H, s), 6.92-7.54(10H,m) Isomer B: mp 106.0-107.0° C. 123 4-CF₃—C₆H₄ Me 1-Me- 1 imidazol-2-yl124 2,4-F₂—C₆H₃ Me 1-Me- 1 imidazol-2-yl 125 2,5-F₂—C₆H₃ Me 1-Me- 1imidazol-2-yl 126 2,6-F₂—C₆H₃ Me 1-Me- 1 imidazol-2-yl 127 3,4-F₂—C₆H₃Me 1-Me- 1 imidazol-2-yl 128 3,5-F₂—C₆H₃ Me 1-Me- 1 imidazol-2-yl 1292,3-Cl₂—C₆H₃ Me 1-Me- 1 imidazol-2-yl 130 2,4-Cl₂—C₆H₃ Me 1-Me- 1 IsomerA: mp 115.0-116.0° C. imidazol-2-yl Isomer B: mp 157.5-158.5° C. 1312,5-Cl₂—C₆H₃ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₂)δ imidazol-2-yl ppm:3.94(3H, s), 3.98(3H, s), 5.04(2H, s), 6.82-7.65(9H, m) Isomer B mp128.5-130.0° C. 132 3,4-Cl₂—C₆H₃ Me 1-Me- 1 Isomer A: ¹H-NMR(CDCl₂)δimidazol-2-yl ppm: 3.91(3H, s), 3.96(3H, s), 4.94(2H, s), 6.67-7.65(9H,m) Isomer B: mp 124.5-125.5° C. 133 3,5-Cl₂—C₆H₃ Me 1-Me- 1imidazol-2-yl 134 2,3-Me₂—C₆H₃ Me 1-Me- 1 imidazol-2-yl 135 2,4-Me₂—C₆H₃Me 1-Me- 1 imidazol-2-yl 136 2,5-Me₂—C₆H₃ Me 1-Me- 1 Isomer A¹H-NMR(CDCl₃)δ imidazol-2-yl ppm: 2.13(3H, s), 2.24(3H, s), 3.86(3H, s),3.97(3H, s), 4.92(2H, s), 6.55(1H, s), 6.63(1H, d, J=7.9), 6.91(1H, s),6.98(1H, d, J=7.9), 7.26(1H, s), 7.29-7.60(4H, m) Isomer B¹H-NMR(CDCl₃)δ ppm: 2.21(3H, s), 2.29(3H, s), 3.49(3H, s), 4.03(3H, s),4.92(2H, s), 6.53(1H, s), 6.67(1H, d, J=7.3), 6.95(1H, d, J=1.2),7.01(1H, d, 7.3), 7.17(1H, d, J=1.2), 7.30- 7.65(4H, m) 137 3,4-Me₂—C₆H₃Me 1-Me- 1 imidazol-2-yl 138 3,5-Me₂—C₆H₃ Me 1-Me- 1 imidazol-2-yl 1392-Cl-4-Me—C₆H₃ Me 1-Me- 1 imidazol-2-yl 140 2-Cl-5-Me—C₆H₃ Me 1-Me- 1imidazol-2-yl 141 4-Cl-2-Me—C₆H₃ Me 1-Me- 1 Isomer A: mp 87.0-88.0° C.imidazol-2-yl Isomer B: mp 134.0-135.0° C. 142 4-Cl-3-Me—C₆H₃ Me 1-Me- 1imidazol-2-yl 143 3-Ph—C₆H₄ Me 1-Me- 1 imidazol-2-yl 144 4-Ph—C₆H₄ Me1-Me- 1 Isomer A: ¹H-NMR(CDCl₃)δ imidazol-2-yl ppm: 3.87(3H, s),3.97(3H, s), 4.98(2H, s), 6.88-7.64(15H, m) Isomer B: mp 141.5-142.5° C.145 3-i-PrO—C₆H₄ Me 1-Me- 1 imidazol-2-yl 146 3-i-Pr—C₆H₄ Me 1-Me- 1Isomer A: ¹H-NMR(CDCl₃)δ imidazol-2-yl ppm: 1.20(6H, d, J=7.3), 2.83(1H,sept, J=7.3), 3.82(3H, s), 3.96(3H, s), 4.91(2H, s), 6.61-7.57(10H, m)Isomer B: ¹H-NMR(CDCl₃)δ ppm: 1.23(6H, d, J=7.3), 2.86(1H, sept, J=7.3),3.50(3H, s), 4.00(3H, s), 4.88(2H, s), 6.64-7.58(10H, m) 147 4-i-Pr—C₆H₄Me 1-Me- 1 imidazol-2-yl 148 3-t-Bu—C₆H₄ Me 1-Me- 1 imidazol-2-yl 1492-MeS—C₆H₄ Me 1-Me- 1 imidazol-2-yl 150 4-MeS—C₆H₄ Me 1-Me- 1imidazol-2-yl 151 2,3,6-F₃—C₆H₂ Me 1-Me- 1 imidazol-2-yl 1522,4,5-Cl₃—C₆H₂ Me 1-Me- 1 imidazol-2-yl 153 3-PhO—C₆H₄ Me 1-Me- 1imidazol-2-yl 154 3,4,5-(MeO₃— Me 1-Me- 1 C₆H₂ imidazol-2-yl 1552,3,5-Me₃—C₆H₂ Me 1-Me- 1 imidazol-2-yl 156 3,4,5-Me₃—C₆H₂ Me 1-Me- 1imidazol-2-yl 157 C₆F₅ Me 1-Me- 1 imidazol-2-yl 158 4-Cl-3-Et—C₆H₃ Me1-Me- 1 imidazol-2-yl 159 3-EtO—C₆H₄ Me 1-Me- 1 imidazol-2-yl 1604-EtO—C₆H₄ Me 1-Me- 1 imidazol-2-yl 161 C₆H₅ Me 1-Me- 0¹H-NMR(CDCl₃)δppm: imidazol-2-yl 3.48(3H, s), 4.02(3H, s), 6.67-7.36(10H, m), 7.75(1H, dd, J=7.3, 1.8) 162 4-F—C₆H₄ Me 1-Me- 0imidazol-2-yl 163 3-Cl—C₆H₄ Me 1-Me- 0 imidazol-2-yl 164 4-Cl—C₆H₄ Me1-Me- 0 imidazol-2-yl 165 3-Me—C₆H₄ Me 1-Me- 0 imidazol-2-yl 1664-Me—C₆H₄ Me 1-Me- 0 imidazol-2-yl 167 4-Et—C₆H₄ Me 1-Me- 0imidazol-2-yl 168 4-NO₂—C₆H₄ Me 1-Me- 0 imidazol-2-yl 169 3,4,-Cl₂—C₆H₃Me 1-Me- 0 imidazol-2-yl 170 3,5-Cl₂—C₆H₃ Me 1-Me- 0 imidazol-2-yl 1713,4-Me₂—C₆H₃ Me 1-Me- 0 imidazol-2-yl 172 3,5-Me₂—C₆H₃ Me 1-Me- 0imidazol-2-yl 173 3-PhO—C₆H₄ Me 1-Me- 0 imidazol-2-yl 174 4-Cl-3-Et—C₆H₃Me 1-Me- 0 imidazol-2-yl 175 3-EtO—C₆H₄ Me 1-Me- 0 imidazol-2-yl 1763-CF₃—C₆H₄ Me 1-Me- 0 imidazol-2-yl 177 4-CF₃—C₆H₄ Me 1-Me- 0imidazol-2-yl 178 3-i-PrO—C₆H₄ Me 1-Me- 0 imidazol-2-yl 179 3-i-Pr—C₆H₄Me 1-Me- 0 imidazol-2-yl 180 4-Cl-3-Me—C₆H₃ Me 1-Me- 0 imidazol-2-yl 181Pyridin-2-yl Me 1-Me- 1 imidazol-2-yl 182 Pyridin-3-yl Me 1-Me- 1imidazol-2-yl 183 5-Cl- Me 1-Me- 1 pyridin-2-yl imidazol-2-yl 184 3-Cl-Me 1-Me- 1 pyridin-2-yl imidazol-2-yl 185 6-Cl- Me 1-Me- 1 pyridin-2-ylimidazol-2-yl 186 2-Cl- Me 1-Me- 1 pyridin-2-yl imidazol-2-yl 187 5-CF₃-Me 1-Me- 1 pyridin-2-yl imidazol-2-yl 188 3-CF₃- Me 1-Me- 1 pyridin-2-ylimidazol-2-yl 189 6-CF₃-3-Cl Me 1-Me- 1 pyridin-2-yl imidazol-2-yl 1905-CF₃-3-Cl Me 1-Me- 1 pyridin-2-yl imidazol-2-yl 191 Benzothiazol- Me1-Me- 1 2-yl imidazol-2-yl 192 Benzoxazol- Me 1-Me- 1 2-yl imidazol-2-yl193 Quinolin-2-yl Me 1-Me- 1 imidazol-2-yl 194 5-CF₃-1,3,4- Me 1-Me- 1thiadiazol-2-yl imidazol-2-yl 195 Pyimidin-2-yl Me 1-Me- 1 imidazol-2-yl196 5-Cl-6-Me- Me 1-Me- 1 pyrimidin-4-yl imidazol-2-yl 197 5-Et-6-Me- Me1-Me- 1 pyrimidin-4-yl imidazol-2-yl 198 6-Cl- Me 1-Me- 1 pyrazin-2-ylimidazol-2-yl 199 3,6-Me₂- Me 1-Me- pyrazin-2-yl imidazol-2-yl 200 5-Me-Me- 1-Me- 1 isoxazol-3-yl imidazol-2-yl 201 C₆H₅ Me 5-Me- 1¹H-NMR(CDCl₃)δppm: imidazol-1-yl 1.95(3H, s), 3.92(3H, s), 5.18(2H, s),6.86-7.71(11H, m) 202 2-F—C₆H₄ Me 5-Me- 1 imidazol-1-yl 203 3-F—C₆H₄ Me5-Me- 1 imidazol-1-yl 204 4-F—C₆H₄ Me 5-Me- 1 imidazol-1-yl 2052-Cl—C₆H₄ Me 5-Me- 1 ¹H-NMR(CDCl₃)δppm: imidazol-1-yl 1.94(3H, d,J=1.2), 3.96(3H, s), 5.24(2H, s), 6.86-7.82(10H, m) 206 3-Cl—C₆H₄ Me5-Me- 1 ¹H-NMR(CDCl₂)δppm: imidazol-1-yl 1.96(3H, s), 3.93(3H, s),5.18(2H, s), 6.79-7.67(10H, m) 207 4-Cl—C₆H₄ Me 5-Me- 1¹H-NMR(CDCl₂)δppm: imidazol-1-yl 1.94(3H, s), 3.92(3H, s), 5.13(2H, s),6.82-7.66(10H, m) 208 2-Me—C₆H₄ Me 5-Me- 1 imidazol-1-yl 209 3-Me—C₆H₄Me 5-Me- 1 imidazol-1-yl 210 4-Me—C₆H₄ Me 5-Me- 1 imidazol-1-yl 2112-MeO—C₆H₄ Me 5-Me- 1 imidazol-1-yl 212 3-MeO—C₆H₄ Me 5-Me- 1imidazol-1-yl 213 4-MeO—C₆H₄ Me 5-Me- 1 imidazol-1-yl 214 2,5-Me₂—C₆H₄Me 5-Me- 1 imidazol-1-yl 215 C₆H₅ Et 5-Me- 1 ¹H-NMR(CDCl₃)δppm:imidazol-1-yl 1.28(3H, t, J=7.3), 1.96(3H, s), 4.19(2H, q, J=7.3),5.20(2H, s), 6.86-7.72(11H, m) 216 4-Cl—C₆H₄ Et 5-Me- 1 imidazol-1-yl217 4-Me—C₆H₄ Et 5-Me- 1 imidazol-1-yl 218 C₆H₅ Allyl 50Me- 1imidazol-1-yl 219 4-Cl—C₆H₄ Me 5-Me- 1 imidazol-1-yl 220 4-Me—C₆H₄ Me5-Me- 1 imidazol-1-yl 221 C₆H₅ Me 4-Me- 1 ¹H-NMR(CDCl₃)δppm:imidazol-1-yl 2.19(3H, s), 3.95(3H, s), 5.00(2H, s), 6.79-7.63(10H, m),7.90(1H, s) 222 2-F—C₆H₄ Me 4-Me- 1 imidazol-1-yl 223 3-F—C₆H₄ Me 4-Me-1 imidazol-1-yl 224 4-F—C₆H₄ Me 4-Me- 1 imidazol-1-yl 225 2-Cl—C₆H₄ Me4-Me- 1 ¹H-NMR(CDCl₃)δppm: imidazol-1-yl 2.18(3H, d, J=1.2), 3.99(3H,s), 5.05(2H, s), 6.77-7.72(9H, m), 7.90(1H, d, J=1.2) 226 3-Cl—C₆H₄ Me4-Me- 1 ¹H-NMR(CDCl₃)δppm: imidazol-1-yl 2.19(3H, s), 3.96(3H, s),4.99(2H, s), 6.95-7.59(9H, m), 7.88(1H, d, J=1.2) 227 4-Cl—C₆H₄ Me 4-Me-1 ¹H-NMR(CDCl₃)δppm: imidazol-1-yl 2.18(3H, s), 3.95(3H, s), 4.97(2H,s), 6.70-7.59(9H, m), 7.88(1H, d, J=1.2) 228 2-Me—C₆H₄ Me 4-Me- 1imidazol-1-yl 229 3-Me—C₆H₄ Me 4-Me- 1 imidazol-1-yl 230 4-Me—C₆H₄ Me4-Me- 1 imidazol-1-yl 231 2-MeO—C₆H₄ Me 4-Me- 1 imidazol-1-yl 2323-MeO—C₆H₄ Me 4-Me- 1 imidazol-1-yl 233 4-MeO—C₆H₄ Me 4-Me- 1imidazol-1-yl 234 2,5-Me₂—C₆H₃ Me 4-Me- 1 imidazol-1-yl 235 C₆H₅ Et4-Me- 1 ¹H-NMR(CDCl₃)δppm: imisazol-1-yl 1.30(3H, t, J=7.3), 2.19(3H,s), 4.21(2H, q, J=7.3), 5.02(2H, s), 6.78-7.63(10H, m), 7.96(1H, s) 2364-Cl—C₆H₄ Et 4-Me- 1 imidazol-1-yl 237 4-Me—C₆H₄ Et 4-Me- 1imidazol-1-yl 238 C₆H₅ Allyl 4-Me- 1 imidazol-1-yl 239 4-Cl—C₆H₄ Allyl4-Me- 1 imidazol-1-yl 240 4-Me—C₆H₄ Allyl 4-Me- 1 imidazol-1-yl 241 C₆H₅Me 2-Me- 1 ¹H-NMR(CDCl₃)δppm: imidazol-1-yl 2.21(3H, s), 3.93(3H, s),5.18(2H, s), 6.86-7.71(11H, m) 242 2-F—C₆H₄ Me 2-Me- 1 imidazol-1-yl 2433-F—C₆H₄ Me 2-Me- 1 imidazol-1-yl 244 4-F—C₆H₄ Me 2-Me- 1 imidazol-1-yl245 2-Cl—C₆H₄ Me 2-Me- 1 imidazol-1-yl 246 3-Cl—C₆H₄ Me 2-Me- 1imidazol-1-yl 247 4-Cl—C₆H₄ Me 2-Me- 1 imidazol-1-yl 248 2-Me—C₆H₄ Me2-Me- 1 imidazol-1-yl 249 3-Me—C₆H₄ Me 2-Me- 1 imidazol-1-yl 2504-Me—C₆H₄ Me 2-Me- 1 imidazol-1-yl 251 2-MeO—C₆H₄ Me 2-Me- 1imidazol-1-yl 252 3-MeO—C₆H₄ Me 2-Me- 1 imidazol-1-yl 253 4-MeO—C₆H₄ Me2-Me- 1 imidazol-1-yl 254 2,5-Me₂—C₆H₃ Me 2-Me- 1 imidazol-1-yl 255 C₆H₅Et 2-Me- 1 imidazol-1-yl 256 4-Cl—C₆H₄ Et 2-Me- 1 imidazol-1-yl 2574-Me—C₆H₄ Et 2-Me- 1 imidazol-1-yl 258 C₆H₅ Allyl 2-Me- 1 imidazol-1-yl259 4-Cl—C₆H₄ Allyl 2-Me- 1 imidazol-1-yl 260 4-Me—C₆H₄ Allyl 2-Me- 1imidazol-1-yl 261 C₆H₅ Me 1H-1,2,4- 1 mp 86-87° C. Triazol-1-yl 2622-F—C₆H₄ Me 1H-1,2,4- 1 Triazol-1-yl 263 3-F—C₆H₄ Me 1H-1,2,4- 1Triazol-1-yl 264 4-F—C₆H₄ Me 1H-1,2,4- 1 Triazol-1-yl 265 2-Cl—C₆H₄ Me1H-1,2,4- 1 mp 101.5-102.5° C. Triazol-1-yl 266 3-Cl—C₆H₄ Me 1H-1,2,4- 1¹H-NMR(CDCl₃)δppm: Triazol-1-yl 4.06(3H, s), 4.94(2H, s), 6.63- 7.65(8H,m), 7.96(1H, s), 9.12(1H, s) 267 4-Cl—C₆H₄ Me 1H-1,2,4- 1 mp 101-102° C.Triazol-1-yl 268 2-Me—C₆H₄ Me 1H-1,2,4- 1 Triazol-1-yl 269 3-Me—C₆H₄ Me1H-1,2,4- 1 Triazol-1-yl 270 4-Me—C₆H₄ Me 1H-1,2,4- 1 mp 98.5-99.5° C.Triazol-1-yl 271 2-MeO—C₆H₄ Me 1H-1,2,4- 1 Triazol-1-yl 272 3-MeO—C₆H₄Me 1H-1,2,4- 1 Triazol-1-yl 273 4-MeO—C₆H₄ Me 1H-1,2,4- 1 Triazol-1-yl274 2,5-Me₂—C₆H₃ Me 1H-1,2,4- 1 mp 96-98° C. Triazol-1-yl 275 C₆H₅ Et1H-1,2,4- 1 mp 78.5-80.5° C. Triazol-1-yl 276 4-Cl—C₆H₄ Et 1H-1,2,4- 1Triazol-1-yl 277 4-Me—C₆H₄ Et 1H-1,2,4- 1 Triazol-1-yl 278 C₆H₅ Allyl1H-1,2,4- 1 ¹H-NMR(CDCl₃)δppm: 4.71- Triazol-1-yl 4.74(2H, m), 4.94(2H,s), 5.25- 5.37(2H, m), 5.91-6.06(1H, m), 6.76-7.59(9H, m), 7.96(1H, s),9.13(1H, s) 279 4-Cl—C₆H₄ Allyl 1H-1,2,4- 1 Triazol-1-yl 280 4-Me—C₆H₄Allyl 1H-1,2,4- 1 Triazol-1-yl 281 C₆H₅ Me Pyrazol-1-yl 1¹H-NMR(CDCl₃)δppm: 4.02(3H, s), 4.78(2H, s), 6.40(1H, dd, J=3.1, 1.8),6.78- 7.62(10H, m), 8.42(1H, d, J=2.4) 282 2-F—C₆H₄ Me Pyrazol-1-yl 1283 3-F—C₆H₄ Me Pyrazol-1-yl 1 284 4-F—C₆H₄ Me Pyrazol-1-yl 1 2852-Cl—C₆H₄ Me Pyrazol-1-yl 1 mp 90-91° C. 286 3-Cl—C₆H₄ Me Pyrazol-1-yl 1¹H-NMR(CDCl₃)δppm: 4.26(3H, s), 4.78(2H, s), 6.42- 7.62(10H, m),8.45(1H, d, J=2.4) 287 4-Cl—C₆H₄ Me Pyrazol-1-yl 1 mp 94-95° C. 2882-Me—C₆H₄ Me Pyrazol-1-yl 1 289 3-Me—C₆H₄ Me Pyrazol-1-yl 1 2904-Me—C₆H₄ Me Pyrazol-1-yl 1 mp 82-83° C. 291 2-Cl- Me Pyrazol-1-yl 1 mp87.5-88.5° C. 292 3-MeO—C₆H₄ Me Pyrazol-1-yl 1 293 4-MeO—C₆H₄ MePyrazol-1-yl 1 294 2,5-Me₂—C₆H₃ Me Pyrazol-1-yl 1 mp 78-80° C. 295 C₆H₅Et Pyrazol-1-yl 1 ¹H-NMR(CDCl₃)δppm: 1.36(3H, t, J=6.7), 4.27(2H, q,J=6.7), 4.79(2H, s), 6.40- 7.61(11H, m) 8.48(1H, d, J=3.1) 296 4-Cl—C₆H₄Et Pyrazol-1-yl 1 297 4-Me—C₆H₄ Et Pyrazol-1-yl 1 298 C₆H₅ AllylPyrazol-1-yl 1 ¹H-NMR(CDCl₃)δppm: 4.73(2H, m), 4.80(2H, s), 5.23-5.38(2H, m), 5.95-6.10(1H, m), 6.40-7.62(11H, m), 8.48(1H, d, J=2.4) 2994-Cl—C₆H₄ Allyl Pyrazol-1-yl 1 300 C₆H₅ Me Pyrazol-1-yl 0¹H-NMR(CDCl₃)δppm: 4.03(3H, s), 6.34(1H, t, J=2.9), 6.82-7.63(10H, m),8.37(1H, d, J=2.9) 301 C₆H₅ Me Isoxazol-3-yl 1 ¹H-NMR(CDCl₃)δppm:4.06(3.99)(3H, s), 5.05(4.96)(2H, s),6.73- 7.61(10H, m), 8.46(8.39)(1H,d, J=1.8) 302 2-F—C₆H₄ Me Isoxazol-3-yl 1 303 3-F—C₆H₄ Me Isoxazol-3-yl1 304 4-F—C₆H₄ Me Isoxazol-3-yl 1 305 2-Cl—C₆H₄ Me Isoxazol-3-yl 1¹H-NMR(CDCl₃)δppm: 4.08(4.01)(3H, s), 5.14(5.12)(2H, s), 6.76- 7.68(9H,m), 8.48(8.40)(1H, d, J=1.8) 306 3-Cl—C₆H₄ Me Isoxazol-3-yl 1¹H-NMR(CDCl₃)δppm: 4.07(4.01)(3H, s), 5.04(4.95)(2H, s), 6.70- 7.56(9H,m), 8.48(8.40)(1H, d, J=1.8) 307 4-Cl—C₆H₄ Me Isoxazol-3-yl 14.06(3.99)(3H, s), 5.03(4.94)(3H, s), 6.72-7.56(9H, m), 8.47(8.39)(1H,d, J= 1.8) 308 2-Br—C₆H₄ Me Isoxazol-3-yl 1 309 3-Br—C₆H₄ MeIsoxazol-3-yl 1 310 4-Br—C₆H₄ Me Isoxazol-3-yl 1 311 3-I—C₆H₄ MeIsoxazol-3-yl 1 312 2-Me—C₆H₄ Me Isoxazol-3-yl 1 ¹H-NMR(CDCl₃)δppm:2.20(2.17)(3H, s), 4.07(4.00)(3H, s), 5.03(4.97)(2H, s), 6.68- 7.64(9H,m), 8.44(8.39)(1H, d, J=1.8) 313 3-Me—C₆H₄ Me Isoxazol-3-yl 1¹H-NMR(CDCl₃)δppm: 2.29(2.27)(3H, s), 4.07(4.00)(3H, s), 5.03(4.95)(2H,s), 6.62- 7.61(9H, m), 8.47(8.39)(1H, d, J=1.8) 314 4-Me—C₆H₄ MeIsoxazol-3-yl 1 ¹H-NMR(CDCl₃)δppm: 2.25(3H, s), 4.06(3.99)(3H, s),5.01(4.93)(2H, s), 6.70- 7.60(9H, m), 8.46(8.39)(1H, d, J=1.8) 3152-Et—C₆H₄ Me Isoxazol-3-yl 1 316 3-Et—C₆H₄ Me Isoxazol-3-yl 1 3174-Et—C₆H₄ Me Isoxazol-3-yl 1 318 2-MeO—C₆H₄ Me Isoxazol-3-yl 1 3193-MeO—C₆H₄ Me Isoxazol-3-yl 1 320 4-MeO—C₆H₄ Me Isoxazol-3-yl 1 3212-CF₃—C₆H₄ Me Isoxazol-3-yl 1 322 3-CF₃—C₆H₄ Me Isoxazol-3-yl 1¹H-NMR(CDCl₃)δppm: 4.05(3.98)(3H, s), 5.10(5.01)(2H, s), 6.74(1H, d,J=1.8), 6.94-7.57(8H, m), 8.47(8.40)(1H, d, J=1.8) 323 4-CF₃—C₆H₄ MeIsoxazol-3-yl 1 324 2,4-F₂—C₆H₃ Me Isoxazol-3-yl 1 325 2,5-F₂—C₆H₃ MeIsoxazol-3-yl 1 326 2,6-F₂—C₆H₃ Me Isoxazol-3-yl 1 327 3,4-F₂—C₆H₃ MeIsoxazol-3-yl 1 328 3,5-F₂—C₆H₃ Me Isoxazol-3-yl 1 329 2,3-Cl₂—C₆H₃ MeIsoxazol-3-yl 1 330 2,4-Cl₂—C₆H₃ Me Isoxazol-3-yl 1 331 2,5-Cl₂—C₆H₃ MeIsoxazol-3-yl 1 332 3,4-Cl₂—C₆H₃ Me Isoxazol-3-yl 1 333 3,5-Cl₂—C₆H₃ MeIsoxazol-3-yl 1 334 2,3-Me₂—C₆H₃ Me Isoxazol-3-yl 1 335 2,4-Me₂—C₆H₃ MeIsoxazol-3-yl 1 336 2,5-Me₂—C₆H₃ Me Isoxazol-3-yl 1 mp 104-108° C. 3373,4-Me₂—C₆H₃ Me Isoxazol-3-yl 1 338 3,5-Me₂—C₆H₃ Me Isoxazol-3-yl 1 3392-Cl-4-Me—C₆H₃ Me Isoxazol-3-yl 1 340 2-Cl-5-Me—C₆H₃ Me Isoxazol-3-yl 1341 4-Cl-2-Me—C₆H₃ Me Isoxazol-3-yl 1 ¹H-NMR(CDCl₃)δppm: 2.16(2.13)(3H,s), 4.07(3.99)(3H, s), 5.01(4.95)(2H, s), 6.59- 7.58(8H, m),8.45(8.40)(1H, d, J=1.8) 342 4-Cl-3-Me—C₆H₃ Me Isoxazol-3-yl 1 3433-Ph—C₆H₄ Me Isoxazol-3-yl 1 344 4-Ph—C₆H₄ Me Isoxazol-3-yl 1 3453-i-PrO—C₆H₄ Me Isoxazol-3-yl 1 346 3-i-Pr—C₆H₄ Me Isoxazol-3-yl 1 3474-i-Pr—C₆H₄ Me Isoxazol-3-yl 1 348 3-t-Bu—C₆H₄ Me Isoxazol-3-yl 1 3492-MeS—C₆H₄ Me Isoxazol-3-yl 1 350 4-MeS—C₆H₄ Me Isoxazol-3-yl 1 3512,3,6-F₃—C₆H₂ Me Isoxazol-3-yl 1 352 2,4,5-Cl₃—C₆H₂ Me Isoxazol-3-yl 1353 3-PhO—C₆H₄ Me Isoxazol-3-yl 1 354 3,4,5-(MeO)₃— Me Isoxazol-3-yl 1C₆H₂ 355 2,3,5-Me₃—C₆H₂ Me Isoxazol-3-yl 1 356 3,4,5-Me₃—C₆H₂ MeIsoxazol-3-yl 1 357 C₆F₅ Me Isoxazol-3-yl 1 358 4-Cl-3-Et—C₆H₃ MeIsoxazol-3-yl 1 359 3-EtO—C₆H₄ Me Isoxazol-3-yl 1 360 4-EtO—C₆H₄ MeIsoxazol-3-yl 1 361 C₆H₅ Me Isoxazol-3-yl 0 362 4-F—C₆H₄ MeIsoxazol-3-yl 0 363 3-Cl—C₆H₄ Me Isoxazol-3-yl 0 364 4-Cl—C₆H₄ MeIsoxazol-3-yl 0 365 3-Me—C₆H₄ Me Isoxazol-3-yl 0 366 4-Me—C₆H₄ MeIsoxazol-3-yl 0 367 4-Et—C₆H₄ Me Isoxazol-3-yl 0 368 4-NO₂—C₆H₄ MeIsoxazol-3-yl 0 369 3,4-Cl₂—C₆H₃ Me Isoxazol-3-yl 0 370 3,5-Cl₂—C₆H₃ MeIsoxazol-3-yl 0 371 3,4-Me₂—C₆H₃ Me Isoxazol-3-yl 0 372 3,5-Me₂—C₆H₃ MeIsoxazol-3-yl 0 373 3-PhO—C₆H₄ Me Isoxazol-3-yl 0 374 4-Cl-3-Et—C₆H₃ MeIsoxazol-3-yl 0 375 3-EtO—C₆H₄ Me Isoxazol-3-yl 0 376 3-CF₃—C₆H₄ MeIsoxazol-3-yl 0 377 4-CF₃—C₆H₄ Me Isoxazol-3-yl 0 378 3-i-PrO—C₆H₄ MeIsoxazol-3-yl 0 379 3-i-Pr—C₆H₄ Me Isoxazol-3-yl 0 380 4-Cl-3-Me—C₆H₃ MeIsoxazol-3-yl 0 381 pyridin-2-yl Me Isoxazol-3-yl 1 382 pyridin-3-yl MeIsoxazol-3-yl 1 383 5-Cl- Me Isoxazol-3-yl 1 pyridin-2-yl 384 3-Cl- MeIsoxazol-3-yl 1 pyridin-2-yl 385 6-Cl- Me Isoxazol-3-yl 1 pyridin-2-yl386 2-Cl- Me Isoxazol-3-yl 1 pyridin-2-yl 387 5-CF₃- Me Isoxazol-3-yl 1¹H-NMR(CDCl₃)δppm: pyridin-2-yl 3.98(3H, s), 5.32(2H, s), 6.63(1H, d,J=8.5), 6.73(1H, d, J=1.8), 7.27-7.71(5H, m), 8.30(1H, s), 8.39(1H, d,J=1.8) 388 3-CF₃- Me Isoxazol-3-yl 1 mp 125-126.5° C. pyridin-2-yl 3896-CF₃-3-Cl- Me Isoxazol-3-yl 1 pyridin-2-yl 390 5-CF₃-3-Cl- MeIsoxazol-3-yl 1 ¹H-NMR(CDCl₃)δ pyridin-2-yl ppm: 4.00(3H, s), 5.41(2H,s), 6.76(1H, d, J=1.8), 7.27- 7.78(5H, m), 8.15(1H, s), 8.46(1H, d,J=1.8) 391 Benzothiazol- Me Isoxazol-3-yl 1 2-yl 392 Benzothiazol- MeIsoxazol-3-yl 1 2-yl 393 Quinolin-2-yl Me Isoxazol-3-yl 1 3945-CF₃-1,3,4- Me Isoxazol-3-yl 1 thiadiazol-2-yl 395 pyrimidin-2-yl MeIsoxazol-3-yl 1 396 5-Cl-6-Me- Me Isoxazol-3-yl 1 pyrimidin-4-yl 3975-Et-6-Me- Me Isoxazol-3-yl 1 pyrimidin-4-yl 398 6-Cl- Me Isoxazol-3-yl1 pyrazin-2-yl 399 3,6-Me₂- Me Isoxazol-3-yl 1 pyrazin-2-yl 400 5-Me- MeIsoxazol-3-yl 1 isoxazol-3-yl 401 C₆H₅ Me 5-Me- 1 2.43(3H, s),3.97(4.04)(3H, s), isoxazol-3-yl 4.96(5.06)(2H, s), 6.35(6.55)(1H, s),6.83- 7.60(9H, m) 402 2-F—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 403 3-F—C₆H₄ Me5-Me- 1 isoxazol-3-yl 404 4-F—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 4052-Cl—C₆H₄ Me 5-Me- 1 ¹H-NMR(CDCl₃)δppm: isoxazol-3-yl 2.44(3H, s),4.07(3.98)(3H, s), 5.15(5.06)(2H, s), 6.38(6.57) (1H, s), 6.78-7.66(8H,m) 406 3-Cl—C₆H₄ Me 5-Me- 1 mp 111.0-123.5° C. isoxazol-3-yl 4074-Cl—C₆H₄ Me 5-Me- 1 mp 74.0-85.0° C. isoxazol-3-yl 408 2-Br—C₆H₄ Me5-Me- 1 isoxazol-3-yl 409 3-Br—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 4104-Br—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 411 3-I—C₆H₄ Me 5-Me- 1 isoxazol-3-yl412 2-Me—C₆H₄ Me 5-Me- 1 ¹H-NMR(CDCl₃)δppm: isoxazol-3-yl 2.20(2.22)(3H,s), 2.42(2.42)(3H, s), 3.98(4.06)(3H, s), 4.97(5.04)(2H, s),6.35(6.53)(1H, s), 6.69- 7.63(8H, m) 413 3-Me—C₆H₄ Me 5-Me- 1 mp92.0-93.0° C. isoxazol-3-yl 414 4-Me—C₆H₄ Me 5-Me- 1 mp 104.0-105.5° C.isoxazol-3-yl 415 2-Et—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 416 3-Et-C₆H₄ Me5-Me- 1 isoxazol-3-yl 417 4-Et—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 4182-MeO—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 419 3-MeO—C₆H₄ Me 5-Me- 1isoxazol-3-yl 420 4-MeO—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 421 2-CF₃—C₆H₄ Me5-Me- 1 isoxazol-3-yl 422 3-CF₃—C₆H₄ Me 5-Me- 1 ¹H-NMR(CDCl₃)δppm:isoxazol-3-yl 2.43(2.44)(3H, s), 4.03(3.97)(3H, s), 5.00(5.09)(2H, s),6.35(1H, s), 6.56(6.57)(1H, s), 7.00- 7H, m) 423 4-CF₃—C₆H₄ Me 5-Me- 1isoxazol-3-yl 424 2,4-F₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 425 2,5-F₂—C₆H₃Me 5-Me- 1 isoxazol-3-yl 426 2,6-F₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 4273,4-F₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 428 3,5-F₂—C₆H₃ Me 5-Me- 1isoxazol-3-yl 429 2,3-Cl₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 430 2,4-Cl₂—C₆H₃Me 5-Me- 1 isoxazol-3-yl 431 2,5-Cl₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 4323,4-Cl₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 433 3,5-Cl₂—C₆H₃ Me 5-Me- 1isoxazol-3-yl 434 2,3-Me₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 435 2,4-Me₂—C₆H₃Me 5-Me- 1 isoxazol-3-yl 436 2,5-Me₂—C₆H₃ Me 5-Me- 1 ¹H-NMR(CDCl₃)δppm:isoxazol-3-yl 2.15(2.16)(3H, s), 2.24(2.25)(3H, s), 2.42(2.43)(3H, s),3.99(4.07)(3H, s), 4.95(5.01)(2H, s), 6.36- 7.64(8H, m) 437 3,4-Me₂—C₆H₃Me 5-Me- 1 isoxazol-3-yl 438 3,5-Me₂—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 4392-Cl-4-Me—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 440 2-Cl-5-Me—C₆H₃ Me 5-Me- 1isoxazol-3-yl 441 4-Cl-2-Me—C₆H₃ Me 5-Me- 1 mp 79-83° C. isoxazol-3-yl442 4-Cl-3-Me—C₆H₃ Me 5-Me- 1 isoxazol-3-yl 443 3-Ph—C₆H₄ Me 5-Me- 1isoxazol-3-yl 444 4-Ph—C₆H₄ Me 5-Me- 1 mp 105.0-115.0° C. isoxazol-3-yl445 3-i-PrO—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 446 3-i-Pr—C₆H₄ Me 5-Me- 1isoxazol-3-yl 447 4-i-Pr—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 448 3-t-Bu—C₆H₄Me 5-Me- 1 isoxazol-3-yl 449 2-MeS—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 4504-MeS—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 451 2,3,6-F₃—C₆H₂ Me 5-Me- 1isoxazol-3-yl 452 2,4,5-Cl₃—C₆H₂ Me 5-Me- 1 isoxazol-3-yl 453 3-PhO—C₆H₄Me 5-Me- 1 isoxazol-3-yl 454 3,4,5-(MeO)₃— Me 5-Me- 1 C₆H₂ isoxazol-3-yl455 2,3,5-Me₃—C₆H₂ Me 5-Me- 1 isoxazol-3-yl 456 3,4,5-Me₃—C₆H₂ Me 5-Me-1 isoxazol-3-yl 457 C₆F₅ Me 5-Me- 1 isoxazol-3-yl 458 4-Cl-3-Et—C₆H₃ Me5-Me- 1 isoxazol-3-yl 459 3-EtO—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 4604-EtO—C₆H₄ Me 5-Me- 1 isoxazol-3-yl 461 C₆H₅ Me 5-Me- 0 isoxazol-3-yl462 4-F—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 463 3-Cl—C₆H₄ Me 5-Me- 0isoxazol-3-yl 464 4-Cl—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 465 3-Me—C₆H₄ Me5-Me- 0 isoxazol-3-yl 466 4-Me—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 4674-Et—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 468 4-NO₂—C₆H₄ Me 5-Me- 0isoxazol-3-yl 469 3,4-Cl₂—C₆H₃ Me 5-Me- 0 isoxazol-3-yl 470 3,5-Cl₂—C₆H₃Me 5-Me- 0 isoxazol-3-yl 471 3,4-Me₂—C₆H₃ Me 5-Me- 0 isoxazol-3-yl 4723,5-Me₂—C₆H₃ Me 5-Me- 0 isoxazol-3-yl 473 3-PhO—C₆H₄ Me 5-Me- 0isoxazol-3-yl 474 4-Cl-3-Et—C₆H₃ Me 5-Me- 0 isoxazol-3-yl 475 3-EtO—C₆H₄Me 5-Me- 0 isoxazol-3-yl 476 3-CF₃—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 4774-CF₃—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 478 3-i-PrO—C₆H₄ Me 5-Me- 0isoxazol-3-yl 479 3-i-Pr—C₆H₄ Me 5-Me- 0 isoxazol-3-yl 4804-Cl-3-Me—C₆H₃ Me 5-Me- 0 isoxazol-3-yl 481 Pyridin-2-yl Me 5-Me- 1isoxazol-3-yl 482 Pyridin-3-yl Me 5-Me- 1 isoxazol-3-yl 483 5-Cl- Me5-Me- 1 pyridin-2-yl isoxazol-3-yl 484 3-Cl- Me 5-Me- 1 ¹H-NMR(CDCl₃)δpyridin-2-yl isoxazol-3-yl ppm: 2.42(3H, s), 3.97(3H, s), 5.35(2H, s),6.35(1H, s), 6.76- 6.81(1H, m), 7.24-7.93(6H, m). 485 6-Cl- Me 5-Me- 1pyridin-2-yl isoxazol-3-yl 486 2-Cl- Me 5-Me- 1 pyridin-3-ylisoxazol-3-yl 487 5-CF₃- Me 5-Me- 1 ¹H-NMR(CDCl₃)δppm: pyridin-2-ylisoxazol-3-yl ppm: 2.43(3H, s), 3.96(3H, s), 5.32(2H, s), 6.34(1H, d,J=1.2), 6.67(1H, d, J=8.5), 7.24-7.72(5H, m), 8.31(1H, s) 488 3-CF₃- Me5-Me- 1 pyridin-2-yl isoxazol-3-yl 489 6-CF₃-3-Cl- Me 5-Me- 1pyridin-2-yl isoxazol-3-yl 490 5-CF₃-3-Cl- Me 5-Me- 1 ¹H-NMR(CDCl₃)δpyridin-2-yl isoxazol-3-yl ppm: 2.43(3H, s), 3.97(2H, s), 5.40(2H, s),6.37(1H, s), 7.25- 8.17(6H, m). 491 Benzothiazol- Me 5-Me- 1 2-ylisoxazol-3-yl 492 Benzothiazol- Me 5-Me- 1 2-yl isoxazol-3-yl 493Quinolin-2-yl Me 5-Me- 1 isoxazol-3-yl 494 5-CF₃-1,3,4- Me 5-Me- 1thiadiazol-2-yl isoxazol-3-yl 495 Pyrimidin-2-yl Me 5-Me- 1isoxazol-3-yl 496 5-Cl-6-Me- Me 5-Me- 1 pyrimidin-4-yl isoxazol-3-yl 4975-Et-6-Me- Me 5-Me- 1 pyrimidin-4-yl isoxazol-3-yl 498 6-Cl- Me 5-Me- 1pyrazin-2-yl isoxazol-3-yl 499 3,6-Me₂- Me 5-Me- 1 pyrazin-2-ylisoxazol-3-yl 500 5-Me- Me 5-Me- 1 isoxazol-3-yl isoxazol-3-yl 501 C₆H₅Me Isoxazol-5-yl 1 502 2-F—C₆H₄ Me Isoxazol-5-yl 1 503 3-F—C₆H₄ MeIsoxazol-5-yl 1 504 4-F—C₆H₄ Me Isoxazol-5-yl 1 505 2-Cl—C₆H₄ MeIsoxazol-5-yl 1 506 3-Cl—C₆H₄ Me Isoxazol-5-yl 1 507 4-Cl—C₆H₄ MeIsoxazol-5-yl 1 Isomer A: ¹H-NMR(CDCl₃)δ ppm: 4.11(3H, s), 4.99(2H, s),6.68-6.73(2H, m), 7.11(1H, d, J=1.8), 7.14-7.18(2H, m), 7.40-7.57(4H,m), 8.34(1H, d, J=1.8) Isomer B: ¹H-NMR(CDCl₃)δ ppm: 4.03(3H, s),4.92(2H, s), 6.21(1H, d, J=1.8), 6.68- 6.74(2H, m), 7.13-7.23(3H, m),7.41-7.61(3H, m), 8.24(1H, d, J=1.8) 508 2-Br—C₆H₄ Me Isoxazol-5-yl 1509 3-Br—C₆H₄ Me Isoxazol-5-yl 1 510 4-Br—C₆H₄ Me Isoxazol-5-yl 1 5113-I—C₆H₄ Me Isoxazol-5-yl 1 512 2-Me—C₆H₄ Me Isoxazol-5-yl 1 Isomer A:mp 71.5-72.5° C. Isomer B: mp 68.0-69.0° C. 513 3-Me—C₆H₄ MeIsoxazol-5-yl 1 514 4-Me—C₆H₄ Me Isoxazol-5-yl 1 515 2-Et—C₆H₄ MeIsoxazol-5-yl 1 516 3-Et—C₆H₄ Me Isoxazol-5-yl 1 517 4-Et—C₆H₄ MeIsoxazol-5-yl 1 518 2-MeO—C₆H₄ Me Isoxazol-5-yl 1 519 3-MeO—C₆H₄ MeIsoxazol-5-yl 1 520 4-MeO—C₆H₄ Me Isoxazol-5-yl 1 521 2-CF₃—C₆H₄ MeIsoxazol-5-yl 1 522 3-CF₃—C₆H₄ Me Isoxazol-5-yl 1 Isomer A:¹H-NMR(CDCl₃)δ ppm: 4.10(3H, s), 5.07(2H, s), 6.91-7.02(2H, m), 7.11(1H,d, J=1.8), 7.15-7.59(6H, m), 8.34(1H, d, J=1.8) Isomer B: ¹H-NMR(CDCl₃)δppm: 4.03(3H, s), 4.99(2H, s), 6.22(1H, d, J=1.8), 6.92- 7.62(8H, m),8.24(1H, d, J=1.8) 523 4-CF₃—C₆H₄ Me Isoxazol-5-yl 1 524 2,4-F₂—C₆H₃ MeIsoxazol-5-yl 1 525 2,5-F₂—C₆H₃ Me Isoxazol-5-yl 1 526 2,6-F₂—C₆H₃ MeIsoxazol-5-yl 1 527 3,4-F₂—C₆H₃ Me Isoxazol-5-yl 1 528 3,5-F₂—C₆H₃ MeIsoxazol-5-yl 1 529 2,3-Cl₂—C₆H₃ Me Isoxazol-5-yl 1 530 2,4-Cl₂—C₆H₃ MeIsoxazol-5-yl 1 531 2,5-Cl₂—C₆H₃ Me Isoxazol-5-yl 1 532 3,4-Cl₂—C₆H₃ MeIsoxazol-5-yl 1 533 3,5-Cl₂—C₆H₃ Me Isoxazol-5-yl 1 534 2,3-Me₂—C₆H₃ MeIsoxazol-5-yl 1 535 2,4-Me₂—C₆H₃ Me Isoxazol-5-yl 1 536 2,5-Me₂—C₆H₃ MeIsoxazol-5-yl 1 Isomer A: mp 137.5-138.5° C. Isomer B: mp 93.0-94.5° C.537 3,4-Me₂—C₆H₃ Me Isoxazol-5-yl 1 538 3,5-Me₂—C₆H₃ Me Isoxazol-5-yl 1539 2-Cl-4-Me—C₆H₃ Me Isoxazol-5-yl 1 540 2-Cl-5-Me—C₆H₃ MeIsoxazol-5-yl 1 541 4-Cl-2-Me—C₆H₃ Me Isoxazol-5-yl 1 Isomer A: mp84.0-85.0° C. Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.16(3H, s), 4.04(3H, s),4.93(2H, s), 6.20(1H, d, J=1.8), 6.62(1H, d, J=8.5), 6.99-7.63(6H, m),8.22(1H, d, J=1.8) 542 4-Cl-3-Me—C₆H₃ Me Isoxazol-5-yl 1 543 3-Ph—C₆H₄Me Isoxazol-5-yl 1 544 4-Ph—C₆H₄ Me Isoxazol-5-yl 1 545 3-i-PrO—C₆H₄ MeIsoxazol-5-yl 1 546 3-i-Pr—C₆H₄ Me Isoxazol-5-yl 1 547 4-i-Pr—C₆H₄ MeIsoxazol-5-yl 1 548 3-t-Bu—C₆H₄ Me Isoxazol-5-yl 1 549 2-MeS—C₆H₄ MeIsoxazol-5-yl 1 550 4-MeS—C₆H₄ Me Isoxazol-5-yl 1 551 2,3,6-F₃—C₆H₂ MeIsoxazol-5-yl 1 552 2,4,5-Cl₃—C₆H₂ Me Isoxazol-5-yl 1 553 3-PhO—C₆H₄ MeIsoxazol-5-yl 1 554 3,4,5-(MeO)₃— Me Isoxazol-5-yl 1 C₆H₂ 5552,3,5-Me₃—C₆H₂ Me Isoxazol-5-yl 1 556 3,4,5-Me₃—C₆H₂ Me Isoxazol-5-yl 1557 C₆F₅ Me Isoxazol-5-yl 1 558 4-Cl-3-Et—C₆H₃ Me Isoxazol-5-yl 1 5593-EtO—C₆H₄ Me Isoxazol-5-yl 1 560 4-EtO—C₆H₄ Me Isoxazol-5-yl 1 561 C₆H₅Me Isoxazol-5-yl 0 562 4-F—C₆H₄ Me Isoxazol-5-yl 0 563 3-Cl—C₆H₄ MeIsoxazol-5-yl 0 564 4-Cl—C₆H₄ Me Isoxazol-5-yl 0 565 3-Me—C₆H₄ MeIsoxazol-5-yl 0 566 4-Me—C₆H₄ Me Isoxazol-5-yl 0 567 4-Et—C₆H₄ MeIsoxazol-5-yl 0 568 4-NO₂—C₆H₄ Me Isoxazol-5-yl 0 569 3,4-Cl₂—C₆H₃ MeIsoxazol-5-yl 0 570 3,5-Cl₂—C₆H₃ Me Isoxazol-5-yl 0 571 3,4-Me₂—C₆H₃ MeIsoxazol-5-yl 0 572 3,5-Me₂—C₆H₃ Me Isoxazol-5-yl 0 573 3-PhO—C₆H₄ MeIsoxazol-5-yl 0 574 4-Cl-3-Et—C₆H₃ Me Isoxazol-5-yl 0 575 3-EtO—C₆H₄ MeIsoxazol-5-yl 0 576 3-CF₃—C₆H₄ Me Isoxazol-5-yl 0 577 4-CF₃—C₆H₄ MeIsoxazol-5-yl 0 578 3-i-PrO—C₆H₄ Me Isoxazol-5-yl 0 579 3-i-Pr—C₆H₄ MeIsoxazol-5-yl 0 580 4-Cl-3-Me—C₆H₃ Me Isoxazol-5-yl 0 581 Pyridin-2-ylMe Isoxazol-5-yl 1 582 Pyridin-3-yl Me Isoxazol-5-yl 1 583 5-Cl- MeIsoxazol-5-yl 1 pyridin-2-yl 584 3-Cl- Me Isoxazol-5-yl 1 pyridin-2-yl585 6-Cl- Me Isoxazol-5-yl 1 pyridin-2-yl 586 2-Cl- Me Isoxazol-5-yl 1pyridin-3-yl 587 5-CF₃- Me Isoxazol-5-yl 1 pyridin-2-yl 588 3-CF₃- MeIsoxazol-5-yl 1 pyridin-2-yl 589 6-CF₃-3-Cl- Me Isoxazol-5-yl 1pyridin-2-yl 590 5-CF₃-3-Cl- Me Isoxazol-5-yl 1 pyridin-2-yl 591Benzothiazol- Me Isoxazol-5-yl 1 2-yl 592 Benzothiazol- Me Isoxazol-5-yl1 2-yl 593 Quinolin-2-yl Me Isoxazol-5-yl 1 594 5-CF₃-1,3,4- MeIsoxazol-5-yl 1 thiadiazol-2-yl 595 Pyrimidin-2-yl Me Isoxazol-5-yl 1596 5-Cl-6-Me- Me Isoxazol-5-yl 1 pyrimidin-4-yl 597 5-Et-6-Me- MeIsoxazol-5-yl 1 pyrimidin-4-yl 598 6-Cl- Me Isoxazol-5-yl 1 pyrazin-2-yl599 3,6-Me₂- Me Isoxazol-5-yl 1 pyrazin-2-yl 600 5-Me- Me Isoxazol-5-yl1 isoxazol-5-yl 601 C₆H₅ Me 3-Me- 1 Isomer A: mp 99.0-100.0° C.isoxazol-5-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.27(3H, s), 4.02(3H, s),4.95(2H, s), 5.99(1H, s), 6.80- 7.65(9H, m) 602 2-F—C₆H₄ Me 3-Me- 1isoxazol-5-yl 603 3-F—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 604 4-F—C₆H₄ Me3-Me- 1 isoxazol-5-yl 605 2-Cl—C₆H₄ Me 3-Me- 1 Isomer A: mp 87.0-88.0°C. isoxazol-5-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.27(3H, s)m, 4.04(3H,s), 5.01(2H, s), 6.02(1H, s), 6.81- 7.74(8H, m) 606 3-Cl—C₆H₄ Me 3-Me- 1Isomer A: ¹H-NMR(CDCl₃)δ isoxazol-5-yl ppm: 2.35(3H, s), 4.10(3H, s),5.00(2H, s), 6.66-6.91(3H, m), 6.94(1H, s), 7.10-7.57(5H, m). Isomer B:¹H-NMR(CDCl₃)δ ppm: 2.28(3H, s), 4.03(3H, s), 4.94(2H, s), 6.01(1H, s),6.68- 7.65(8H, m) 607 4-Cl—C₆H₄ Me 3-Me- 1 Isomer A: mp 110.0-111.0° C.isoxazol-5-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.27(3H, s), 4.01(3H, s),4.92(2H, s), 5.99(1H, s), 6.71- 7.60(8H, m) 608 2-Br—C₆H₄ Me 3-Me- 1isoxazol-5-yl 609 3-Br—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 610 4-Br—C₆H₄ Me3-Me- 1 isoxazol-5-yl 611 3-I—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 6122-Me—C₆H₄ Me 3-Me- 1 Isomer A: mp 80.0-81.0° C. isoxazol-5-yl Isomer B:¹H-NMR(CDCl₃)δ ppm: 2.17(3H, s), 2.26(3H, s), 4.03(3H, s), 4.93(2H, s),5.98(1H, s), 6.71-7.68(8H, m) 613 3-Me—C₆H₄ Me 3-Me- 1 Isomer A: mp109.0-110.0° C. isoxazol-5-yl Isomer B: mp 94.5-95.5° C. 614 4-Me—C₆H₄Me 3-Me- 1 Isomer A: mp 126.0-127.0° C. isoxazol-5-yl Isomer B:¹H-NMR(CDCl₃)δ ppm: 2.25(3H, s), 2.27(3H, s), 4.02(3H, s), 4.92(2H, s),5.99(1H, s), 6.70-7.64(8H, m) 615 2-Et—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 6163-Et—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 617 4-Et—C₆H₄ Me 3-Me- 1isoxazol-5-yl 618 2-MeO—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 619 3-MeO—C₆H₄ Me3-Me- 1 isoxazol-5-yl 620 4-MeO—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 6212-CF₃—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 622 3-CF₃—C₆H₄ Me 3-Me- 1 Isomer A:¹H-NMR(CDCl₃)δ isoxazol-5-yl ppm: 2.34(3H, s), 4.08(3H, s), 5.05(2H, s),6.92(1H, s), 6.94- 7.57(8H, m) Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.27(3H,s), 4.02(3H, s), 4.99(2H, s), 6.01(1H, s), 6.96- 7.61(8H, m) 6234-CF₃—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 624 2,4-F₂—C₆H₃ Me 3-Me- 1isoxazol-5-yl 625 2,5-F₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 626 2,6-F₂—C₆H₃Me 3-Me- 1 isoxazol-5-yl 627 3,4-F₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 6283,5-F₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 629 2,3-Cl₂—C₆H₃ Me 3-Me- 1isoxazol-5-yl 630 2,4-Cl₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 631 2,5-Cl₂—C₆H₃Me 3-Me- 1 isoxazol-5-yl 632 3,4-Cl₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 6333,5-Cl₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 634 2,3-Me₂—C₆H₃ Me 3-Me- 1isoxazol-5-yl 635 2,4-Me₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 636 2,5-Me₂—C₆H₃Me 3-Me- 1 Isomer Amp 113-114° C. isoxazol-5-yl Isomer Bmp 107-108° C.637 3,4-Me₂—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 638 3,5-Me₂—C₆H₃ Me 3-Me- 1isoxazol-5-yl 639 2-Cl-4-Me—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 6402-Cl-5-Me—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 641 4-Cl-2-Me—C₆H₃ Me 3-Me- 1Isomer A: mp 76.5-77.5° C. isoxazol-5-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm:2.12(3H, s), 2.26(3H, s), 4.03(3H, s), 4.93(2H, s), 5.97(1H, s),6.62(1H, d, J=8.5), 6.99-7.62(6H, m) 642 4-Cl-3-Me—C₆H₃ Me 3-Me- 1isoxazol-5-yl 643 3-Ph—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 644 4-Ph—C₆H₄ Me3-Me- 1 Isomer A: mp 130.5-131.5° C. isoxazol-5-yl Isomer B: mp102.5-103.5° C. 645 3-i-PrO—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 6463-i-Pr—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 647 4-i-Pr—C₆H₄ Me 3-Me- 1isoxazol-5-yl 648 3-t-Bu—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 649 2-MeS—C₆H₄ Me3-Me- 1 isoxazol-5-yl 650 4-MeS—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 6512,3,6-F₃—C₆H₂ Me 3-Me- 1 isoxazol-5-yl 652 2,4,5-Cl₃—C₆H₂ Me 3-Me- 1isoxazol-5-yl 653 3-PhO—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 654 3,4,5-(MeO)₃—Me 3-Me- 1 C₆H₂ isoxazol-5-yl 655 2,3,5-Me₃—C₆H₂ Me 3-Me- 1isoxazol-5-yl 656 3,4,5-Me₃—C₆H₂ Me 3-Me- 1 isoxazol-5-yl 657 C₆F₅ Me3-Me- 1 isoxazol-5-yl 658 4-Cl-3-Et—C₆H₃ Me 3-Me- 1 isoxazol-5-yl 6593-EtO—C₆H₄ Me 3-Me- 1 isoxazol-5-yl 660 4-EtO—C₆H₄ Me 3-Me- 1isoxazol-5-yl 661 C₆H₅ Me 3-Me- 0 Isomer A: mp 100.0-105.5° C.isoxazol-5-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm: 2.28(3H, s), 3.94(3H, s),6.17(1H, s), 6.92-7.41(9H, m) 662 4-F—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 6633-Cl—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 664 4-Cl—C₆H₄ Me 3-Me- 0isoxazol-5-yl 665 3-Me—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 666 4-Me—C₆H₄ Me3-Me- 0 isoxazol-5-yl 667 4-Et—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 6684-NO₂—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 669 3,4-Cl₂—C₆H₃ Me 3-Me- 0isoxazol-5-yl 670 3,5-Cl₂—C₆H₃ Me 3-Me- 0 isoxazol-5-yl 671 3,4-Me₂—C₆H₃Me 3-Me- 0 isoxazol-5-yl 672 3,5-Me₂—C₆H₃ Me 3-Me- 0 isoxazol-5-yl 6733-PhO—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 674 4-Cl-3-Et—C₆H₃ Me 3-Me- 0isoxazol-5-yl 675 3-EtO—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 676 3-CF₃—C₆H₄ Me3-Me- 0 isoxazol-5-yl 677 4-CF₃—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 6783-i-PrO—C₆H₄ Me 3-Me- 0 isoxazol-5-yl 679 3-i-Pr—C₆H₄ Me 3-Me- 0isoxazol-5-yl 680 4-Cl-3-Me—C₆H₃ Me 3-Me- 0 isoxazol-5-yl 681Pyridin-2-yl Me 3-Me- 1 isoxazol-5-yl 682 Pyridin-3-yl Me 3-Me- 1isoxazol-5-yl 683 5-Cl- Me 3-Me- 1 pyridin-2-yl isoxazol-5-yl 684 3-Cl-Me 3-Me- 1 pyridin-2-yl isoxazol-5-yl 685 6-Cl- Me 3-Me- 1 pyridin-2-ylisoxazol-5-yl 686 2-Cl- Me 3-Me- 1 pyridin-3-yl isoxazol-5-yl 687 5-CF₃-Me 3-Me- 1 Isomer A: mp 88.0-90.0° C. pyridin-2-yl isoxazol-5-yl IsomerB: ¹H-NMR(CDCl₃)δ ppm: 2.28(3H, s), 4.01(3H, s), 5.32(2H, s), 6.00(1H,s), 6.64(1H, d, J=9.2), 7.22- 7.73(5H, m), 8.30(1H, d, J=1.2) 688 3-CF₃-Me 3-Me- 1 pyridin-2-yl isoxazol-5-yl 689 6-CF₃-3-Cl- Me 3-Me- 1pyridin-2-yl isoxazol-5-yl 690 5-CF₃-3-Cl- Me 3-Me- 1 Isomer A: mp77.0-79.0° C. pyridin-2-yl isoxazol-5-yl Isomer B: ¹H-NMR(CDCl₃)δ ppm:2.27(3H, s), 4.03(3H, s), 5.39(2H, s), 6.02(1H, s), 7.22- 7.67(4H, m),7.79(1H, d, J=1.8), 8.17(1H, d, J=1.8) 691 Benzothiazol- Me 3-Me- 1 2-ylisoxazol-5-yl 692 Benzothiazol- Me 3-Me- 1 2-yl isoxazol-5-yl 693Quinolin-2-yl Me 3-Me- 1 isoxazol-5-yl 694 5-CF₃-1,3,4- Me 3-Me- 1thiadiazol-2-yl isoxazol-5-yl 695 Pyrimidin-2-yl Me 3-Me- 1isoxazol-5-yl 696 5-Cl-6-Me- Me 3-Me- 1 pyrimidin-4-yl isoxazol-5-yl 6975-Et-6-Me- Me 3-Me- 1 pyrimidin-4-yl isoxazol-5-yl 698 6-Cl- Me 3-Me- 1pyrazin-2-yl isoxazol-5-yl 699 3,6-Me₂- Me 3-Me- 1 pyrazin-2-ylisoxazol-5-yl 700 5-Me- Me 3-Me- 1 isoxazol-5-yl isoxazol-5-yl 701 C₆H₅Me 1,3,4-Oxadiazol-2- 1 mp 88.0-89.0° C. yl 702 2-F—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 703 3-F—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7044-F—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 705 2-Cl—C₆H₄ Me 1,3,4-Oxadiazol-2-1 mp 120.0-121.0° C. yl 706 3-Cl—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 mp97.0-98.0° C. yl 707 4-Cl—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 mp 120-122° C. yl708 2-Br—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 709 3-Br—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 710 4-Br—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7113-I—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 712 2-Me—C₆H₄ Me 1,3,4-Oxadiazol-2-1 mp 95-96.5° C. yl 713 3-Me—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 mp 78.5-79.5°C. yl 714 4-Me—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 715 2-Et—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 716 3-Et—C₆H₄ Me 1,3,4-Oxadiazol-2- 1¹H-NMR(CDCl₃)δppm: yl 1.14(3H, t, J=7.3), 2.56(2H, q, J=7.3), 4.08(3H,s), 4.99(2H, s), 6.73-7.65(8H, m), 8.43(1H, s) 717 4-Et—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 718 2-MeO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 mp85.0-96.5° C. yl 719 3-MeO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7204-MeO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 721 2-CF₃—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 722 3-CF₃—C₆H₄ Me 1,3,4-Oxadiazol-2- 1¹H-NMR(CDCl₃)δppm: yl 4.06(3H, s), 5.03(2H, s), 6.92- 7.59(8H, m),8.44(1H, s) 723 4-CF₃—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 724 2,4-F₂—C₆H₃ Me1,3,4-Oxadiazol-2- 1 yl 725 2,5-F₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 7262,6-F₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 727 3,4-F₂—C₆H₃ Me1,3,4-Oxadiazol-2- 1 yl 728 3,5-F₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 7292,3-Cl₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 730 2,4-Cl₂—C₆H₃ Me1,3,4-Oxadiazol-2- 1 yl 731 2,5-Cl₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 mp152.0-153.0° C. yl 732 3,4-Cl₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1¹H-NMR(CDCl₃)δppm: yl 4.08(3H, s), 4.96(2H, s), 6.63(1H, dd, J=2.4,8.5), 6.89(1H, d, J=3.1), 7.24- 7.57(5H, m), 8.46(1H, s) 7333,5-Cl₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 734 2,3-Me₂—C₆H₃ Me1,3,4-Oxadiazol-2- 1 yl 735 2,4-Me₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 7362,5-Me₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 mp 134-135° C. yl 737 3,4-Me₂—C₆H₃Me 1,3,4-Oxadiazol-2- 1 yl 738 3,5-Me₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl739 2-Cl-4-Me—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 740 2-Cl-5-Me—C₆H₃ Me1,3,4-Oxadiazol-2- 1 yl 741 4-Cl-2-Me—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 mp85.5-86.5° C. yl 742 4-Cl-3-Me—C₆H₃ Me 1,3,4-Oxadiazol-2- 1 yl 7433-Ph—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 744 4-Ph—C₆H₄ Me 1,3,4-Oxadiazol-2-1 yl 745 3-i-PrO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 746 3-i-Pr—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 747 4-i-Pr—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7483-t-Bu—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 749 2-MeS—C₆H₄ Me1,3,4-Oxadiazol-2- 1 yl 750 4-MeS—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7512,3,6-F₃—C₆H₂ Me 1,3,4-Oxadiazol-2- 1 yl 752 2,4,5-Cl₃—C₆H₂ Me1,3,4-Oxadiazol-2- 1 yl 753 3-PhO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7543,4,5-(MeO)₃— Me 1,3,4-Oxadiazol-2- 1 C₆H₂ yl 755 2,3,5-Me₃—C₆H₂ Me1,3,4-Oxadiazol-2- 1 yl 756 3,4,5-Me₃—C₆H₂ Me 1,3,4-Oxadiazol-2- 1 yl757 C₆F₅ Me 1,3,4-Oxadiazol-2- 1 yl 758 4-Cl-3-Et—C₆H₃ Me1,3,4-Oxadiazol-2- 1 yl 759 3-EtO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 7604-EtO—C₆H₄ Me 1,3,4-Oxadiazol-2- 1 yl 761 C₆H₅ Me 1,3,4-Oxadiazol-2- 0yl 762 4-F—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 763 3-Cl—C₆H₄ Me1,3,4-Oxadiazol-2- 0 yl 764 4-Cl—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 7653-Me—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 766 4-Me—C₆H₄ Me 1,3,4-Oxadiazol-2-0 yl 767 4-Et—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 768 4-NO₂—C₆H₄ Me1,3,4-Oxadiazol-2- 0 yl 769 3,4-Cl₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 0 yl 7703,5-Cl₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 0 yl 771 3,4-Me₂—C₆H₃ Me1,3,4-Oxadiazol-2- 0 yl 772 3,5-Me₂—C₆H₃ Me 1,3,4-Oxadiazol-2- 0 yl 7733-PhO—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 774 4-Cl-3-Et—C₆H₃ Me1,3,4-Oxadiazol-2- 0 yl 775 3-EtO—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 7763-CF₃—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 777 4-CF₃—C₆H₄ Me1,3,4-Oxadiazol-2- 0 yl 778 3-i-PrO—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 7793-i-Pr—C₆H₄ Me 1,3,4-Oxadiazol-2- 0 yl 780 4-Cl-3-Me—C₆H₃ Me1,3,4-Oxadiazol-2- 0 yl 781 Pyridin-2-yl Me 1,3,4-Oxadiazol-2- 1 yl 782Pyridin-3-yl Me 1,3,4-Oxadiazol-2- 1 yl 783 5-Cl- Me 1,3,4-Oxadiazol-2-1 pyridin-2-yl yl 784 3-Cl- Me 1,3,4-Oxadiazol-2- 1 pyridin-2-yl yl 7856-Cl- Me 1,3,4-Oxadiazol-2- 1 pyridin-2-yl yl 786 2-Cl- Me1,3,4-Oxadiazol-2- 1 pyridin-3-yl yl 787 5-CF₃- Me 1,3,4-Oxadiazol-2- 1pyridin-2-yl yl 788 3-CF₃- Me 1,3,4-Oxadiazol-2- 1 pyridin-2-yl yl 7896-CF₃-3-Cl- Me 1,3,4-Oxadiazol-2- 1 pyridin-2-yl yl 790 5-CF₃-3-Cl- Me1,3,4-Oxadiazol-2- 1 pyridin-2-yl yl 791 Benzothiazol- Me1,3,4-Oxadiazol-2- 1 2-yl yl 792 Benzothiazol- Me 1,3,4-Oxadiazol-2- 12-yl yl 793 Quinolin-2-yl Me 1,3,4-Oxadiazol-2- 1 yl 794 5-CF₃-1,3,4- Me1,3,4-Oxadiazol-2- 1 thiadiazol-2-yl yl 795 Pyrimidin-2-yl Me1,3,4-Oxadiazol-2- 1 yl 796 5-Cl-6-Me- Me 1,3,4-Oxadiazol-2- 1pyrimidin-4-yl yl 797 5-Et-6-Me- Me 1,3,4-Oxadiazol-2- 1 pyrimidin-4-ylyl 798 6-Cl- Me 1,3,4-Oxadiazol-2- 1 pyrazin-2-yl yl 799 3,6-Me₂- Me1,3,4-Oxadiazol-2- 1 pyrazin-2-yl yl 800 5-Me- Me 1,3,4-Oxadiazol-2- 1isoxazol-3-yl yl 801 C₆H₅ Me 1,2,4-Oxadiazol-3-yl 1 mp 70.5-71.5° C. 8022-F—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 803 3-F—C₆H₄ Me 1,2,4-Oxadiazol-3-yl1 804 4-F—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 805 2-Cl—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 mp 139.0-140.0° C. 806 3-Cl—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 807 4-Cl—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 mp107-108° C. 808 2-Br—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 809 3-Br—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 810 4-Br—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8113-I—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 812 2-Me—C₆H₄ Me 1,2,4-Oxadiazol-3-yl1 mp 79-80° C. 813 3-Me—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 814 4-Me—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 mp 92.5-93.5° C. 815 2-Et—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 816 3-Et—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8174-Et—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 818 2-MeO—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 819 3-MeO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8204-MeO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 821 2-CF₃—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 822 3-CF₃—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8234-CF₃—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 824 2,4-F₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 825 2,5-F₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 8262,6-F₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 827 3,4-F₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 828 3,5-F₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 8292,3-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 830 2,4-Cl₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 831 2,5-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 8323,4-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 833 3,5-Cl₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 834 2,3-Me₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 8352,4-Me₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 836 2,5-Me₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 Isomer A: mp 116.5-117.5° C. Isomer B: mp 69-71°C. 837 3,4-Me₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 838 3,5-Me₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 839 2-Cl-4-Me—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 8402-Cl-5-Me—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 841 4-Cl-2-Me—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 mp 127-128° C. 842 4-Cl-3-Me—C₆H₃ Me1,2,4-Oxadiazol-3-yl 1 843 3-Ph—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8444-Ph—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 mp 147.5-148.5° C. 845 3-i-PrO—C₆H₄Me 1,2,4-Oxadiazol-3-yl 1 846 3-i-Pr—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8474-i-Pr—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 848 3-t-Bu—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 849 2-MeS—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 8504-MeS—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 851 2,3,6-F₃—C₆H₂ Me1,2,4-Oxadiazol-3-yl 1 852 2,4,5-Cl₃—C₆H₂ Me 1,2,4-Oxadiazol-3-yl 1 8533-PhO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 854 3,4,5-(MeO)₃— Me1,2,4-Oxadiazol-3-yl 1 C₆H₂ 855 2,3,5-Me₃—C₆H₂ Me 1,2,4-Oxadiazol-3-yl 1856 3,4,5-Me₃—C₆H₂ Me 1,2,4-Oxadiazol-3-yl 1 857 C₆F₅ Me1,2,4-Oxadiazol-3-yl 1 858 4-Cl-3-Et—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 1 8593-EtO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 1 860 4-EtO—C₆H₄ Me1,2,4-Oxadiazol-3-yl 1 861 C₆H₅ Me 1,2,4-Oxadiazol-3-yl 0 862 4-F—C₆H₄Me 1,2,4-Oxadiazol-3-yl 0 863 3-Cl—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 8644-Cl—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 865 3-Me—C₆H₄ Me1,2,4-Oxadiazol-3-yl 0 866 4-Me—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 8674-Et—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 868 4-NO₂—C₆H₄ Me1,2,4-Oxadiazol-3-yl 0 869 3,4-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 0 8703,5-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 0 871 3,4-Me₂—C₆H₃ Me1,2,4-Oxadiazol-3-yl 0 872 3,5-Me₂—C₆H₃ Me 1,2,4-Oxadiazol-3-yl 0 8733-PhO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 874 4-Cl-3-Et—C₆H₃ Me1,2,4-Oxadiazol-3-yl 0 875 3-EtO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 8763-CF₃—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 877 4-CF₃—C₆H₄ Me1,2,4-Oxadiazol-3-yl 0 878 3-i-PrO—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 8793-i-Pr—C₆H₄ Me 1,2,4-Oxadiazol-3-yl 0 880 4-Cl-3-Me—C₆H₃ Me1,2,4-Oxadiazol-3-yl 0 881 Pyridin-2-yl Me 1,2,4-Oxadiazol-3-yl 1 882Pyridin-3-yl Me 1,2,4-Oxadiazol-3-yl 1 883 5-Cl- Me 1,2,4-Oxadiazol-3-yl1 pyridin-2-yl 884 3-Cl- Me 1,2,4-Oxadiazol-3-yl 1 pyridin-2-yl 8856-Cl- Me 1,2,4-Oxadiazol-3-yl 1 pyridin-2-yl 886 2-Cl- Me1,2,4-Oxadiazol-3-yl 1 mp 177-178.5° C. pyridin-3-yl 887 5-CF₃- Me1,2,4-Oxadiazol-3-yl 1 pyridin-2-yl 888 3-CF₃- Me 1,2,4-Oxadiazol-3-yl 1pyridin-2-yl 889 6-CF₃-3-Cl- Me 1,2,4-Oxadiazol-3-yl 1 pyridin-2-yl 8905-CF₃-3-Cl- Me 1,2,4-Oxadiazol-3-yl 1 pyridin-2-yl 891 Benzothiazol- Me1,2,4-Oxadiazol-3-yl 1 2-yl 892 Benzothiazol- Me 1,2,4-Oxadiazol-3-yl 12-yl 893 Quinolin-2-yl Me 1,2,4-Oxadiazol-3-yl 1 894 5-CF₃-1,3,4- Me1,2,4-Oxadiazol-3-yl 1 thiadiazol-2-yl 895 Pyrimidin-2-yl Me1,2,4-Oxadiazol-3-yl 1 896 5-Cl-6-Me- Me 1,2,4-Oxadiazol-3-yl 1pyrimidin-4-yl 897 5-Et-6-Me- Me 1,2,4-Oxadiazol-3-yl 1 pyrimidin-4-yl898 6-Cl- Me 1,2,4-Oxadiazol-3-yl 1 pyrazin-2-yl 899 3,6-Me₂- Me1,2,4-Oxadiazol-3-yl 1 pyrazin-2-yl 900 5-Me- Me 1,2,4-Oxadiazol-3-yl 1isoxazol-5-yl 901 C₆H₅ Me 5-Me-1,2,4- 1 ¹H-NMR(CDCl₃)δppm:oxadiazol-3-yl 2.64(3H, s), 4.07(3H, s), 4.98(2H, s), 6.82-6.94(2H, m),7.18-7.63(7H, m) 902 2-F—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9033-F—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 904 4-F—C₆H₄ Me 5-Me-1,2,4- 1oxadiazol-3-yl 905 2-Cl—C₆H₄ Me 5-Me-1,2,4- 1 mp 88.5-89.5° C.oxadiazol-3-yl 906 3-Cl—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9074-Cl—C₆H₄ Me 5-Me-1,2,4- 1 mp 125-126° C. oxadiazol-3-yl 908 2-Br—C₆H₄Me 5-Me-1,2,4- 1 oxadiazol-3-yl 909 3-Br—C₆H₄ Me 5-Me-1,2,4- 1oxadiazol-3-yl 910 4-Br—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9113-I—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 912 2-Me—C₆H₄ Me 5-Me-1,2,4- 1mp 86-87.5° C. oxadiazol-3-yl 913 3-Me—C₆H₄ Me 5-Me-1,2,4- 1oxadiazol-3-yl 914 4-Me—C₆H₄ Me 5-Me-1,2,4- 1 mp 92.5-93.5° C.oxadiazol-3-yl 915 2-Et—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9163-Et—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 917 4-Et—C₆H₄ Me 5-Me-1,2,4- 1oxadiazol-3-yl 918 2-MeO—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9193-MeO—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 920 4-MeO—C₆H₄ Me 5-Me-1,2,4-1 oxadiazol-3-yl 921 2-CF₃—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9223-CF₃—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 923 4-CF₃—C₆H₄ Me 5-Me-1,2,4-1 oxadiazol-3-yl 924 2,4-F₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9252,5-F₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 926 2,6-F₂—C₆H₃ Me5-Me-1,2,4- 1 oxadiazol-3-yl 927 3,4-F₂—C₆H₃ Me 5-Me-1,2,4- 1oxadiazol-3-yl 928 3,5-F₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9292,3-Cl₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 930 2,4-Cl₂—C₆H₃ Me5-Me-1,2,4- 1 oxadiazol-3-yl 931 2,5-Cl₂—C₆H₃ Me 5-Me-1,2,4- 1oxadiazol-3-yl 932 3,4-Cl₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9333,5-Cl₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 934 2,3-Me₂—C₆H₃ Me5-Me-1,2,4- 1 oxadiazol-3-yl 935 2,4-Me₂—C₆H₃ Me 5-Me-1,2,4- 1oxadiazol-3-yl 936 2,5-Me₂—C₆H₃ Me 5-Me-1,2,4- 1 Isomer A mp 98-100° C.oxadiazol-3-yl Isomer B mp 130-131.5° C. 937 3,4-Me₂—C₆H₃ Me 5-Me-1,2,4-1 oxadiazol-3-yl 938 3,5-Me₂—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9392-Cl-4-Me—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 940 2-Cl-5-Me—C₆H₃ Me5-Me-1,2,4- 1 oxadiazol-3-yl 941 4-Cl-2-Me—C₆H₃ Me 5-Me-1,2,4- 1 mp115-116° C. oxadiazol-3-yl 942 4-Cl-3-Me—C₆H₃ Me 5-Me-1,2,4- 1oxadiazol-3-yl 943 3-Ph—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9444-Ph—C₆H₄ Me 5-Me-1,2,4- 1 mp 124.5-125.5° C. oxadiazol-3-yl 9453-i-PrO—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 946 3-i-Pr—C₆H₄ Me5-Me-1,2,4- 1 oxadiazol-3-yl 947 4-i-Pr—C₆H₄ Me 5-Me-1,2,4- 1oxadiazol-3-yl 948 3-t-Bu—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9492-MeS—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 950 4-MeS—C₆H₄ Me 5-Me-1,2,4-1 oxadiazol-3-yl 951 2,3,6-F₃—C₆H₂ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9522,4,5-Cl₃—C₆H₂ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 953 3-PhO—C₆H₄ Me5-Me-1,2,4- 1 oxadiazol-3-yl 954 3,4,5-(MeO)₃— Me 5-Me-1,2,4- 1 C₆H₂oxadiazol-3-yl 955 2,3,5-Me₃—C₆H₂ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9563,4,5-Me₃—C₆H₂ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 957 C₆F₅ Me 5-Me-1,2,4- 1oxadiazol-3-yl 958 4-Cl-3-Et—C₆H₃ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9593-EtO—C₆H₄ Me 5-Me-1,2,4- 1 oxadiazol-3-yl 960 4-EtO—C₆H₄ Me 5-Me-1,2,4-1 oxadiazol-3-yl 961 C₆H₅ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 962 4-F—C₆H₄Me 5-Me-1,2,4- 0 oxadiazol-3-yl 963 3-Cl—C₆H₄ Me 5-Me-1,2,4- 0oxadiazol-3-yl 964 4-Cl—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 9653-Me—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 966 4-Me—C₆H₄ Me 5-Me-1,2,4- 0oxadiazol-3-yl 967 4-Et—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 9684-NO₂—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 969 3,4-Cl₂—C₆H₃ Me5-Me-1,2,4- 0 oxadiazol-3-yl 970 3,5-Cl₂—C₆H₃ Me 5-Me-1,2,4- 0oxadiazol-3-yl 971 3,4-Me₂—C₆H₃ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 9723,5-Me₂—C₆H₃ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 973 3-PhO—C₆H₄ Me5-Me-1,2,4- 0 oxadiazol-3-yl 974 4-Cl-3-Et—C₆H₃ Me 5-Me-1,2,4- 0oxadiazol-3-yl 975 3-EtO—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 9763-CF₃—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 977 4-CF₃—C₆H₄ Me 5-Me-1,2,4-0 oxadiazol-3-yl 978 3-i-PrO—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 9793-i-Pr—C₆H₄ Me 5-Me-1,2,4- 0 oxadiazol-3-yl 980 4-Cl-3-Me—C₆H₃ Me5-Me-1,2,4- 0 oxadiazol-3-yl 981 Pyridin-2-yl Me 5-Me-1,2,4- 1oxadiazol-3-yl 982 Pyridin-3-yl Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9835-Cl- Me 5-Me-1,2,4- 1 pyridin-2-yl oxadiazol-3-yl 984 3-Cl- Me5-Me-1,2,4- 1 pyridin-2-yl oxadiazol-3-yl 985 6-Cl- Me 5-Me-1,2,4- 1pyridin-2-yl oxadiazol-3-yl 986 2-Cl- Me 5-Me-1,2,4- 1 mp 82.5-84.5° C.pyridin-3-yl oxadiazol-3-yl 987 5-CF₃- Me 5-Me-1,2,4- 1 pyridin-2-yloxadiazol-3-yl 988 3-CF₃- Me 5-Me-1,2,4- 1 pyridin-2-yl oxadiazol-3-yl989 6-CF₃-3-Cl- Me 5-Me-1,2,4- 1 pyridin-2-yl oxadiazol-3-yl 9905-CF₃-3-Cl- Me 5-Me-1,2,4- 1 pyridin-2-yl oxadiazol-3-yl 991Benzothiazol- Me 5-Me-1,2,4- 1 2-yl oxadiazol-3-yl 992 Benzothiazol- Me5-Me-1,2,4- 1 2-yl oxadiazol-3-yl 993 Quinolin-2-yl Me 5-Me-1,2,4- 1oxadiazol-3-yl 994 5-CF₃-1,3,4- Me 5-Me-1,2,4- 1 thiadiazol-2-yloxadiazol-3-yl 995 Pyrimidin-2-yl Me 5-Me-1,2,4- 1 oxadiazol-3-yl 9965-Cl-6-Me- Me 5-Me-1,2,4- 1 pyrimidin-4-yl oxadiazol-3-yl 997 5-Et-6-Me-Me 5-Me-1,2,4- 1 pyrimidin-4-yl oxadiazol-3-yl 998 6-Cl- Me 5-Me-1,2,4-1 pyrazin-2-yl oxadiazol-3-yl 999 3,6-Me₂- Me 5-Me-1,2,4- 1 pyrazin-2-yloxadiazol-3-yl 1000 5-Me- Me 5-Me-1,2,4- 1 isoxazol-3-yl oxadiazol-3-yl1001 C₆H₅ Me 1-Me-1H- 1 mp 83.0-84.5° C. tetrazol-5-yl 1002 2-F—C₆H₄ Me1-Me-1H- 1 tetrazol-5-yl 1003 3-F—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 10044-F—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1005 2-Cl—C₆H₄ Me 1-Me-1H- 1 mp118-119° C. tetrazol-5-yl 1006 3-Cl—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl1007 4-Cl—C₆H₄ Me 1-Me-1H- 1 mp 95-96° C. tetrazol-5-yl 1008 2-Br—C₆H₄Me 1-Me-1H- 1 tetrazol-5-yl 1009 3-Br—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl1010 4-Br—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1011 3-I—C₆H₄ Me 1-Me-1H- 1tetrazol-5-yl 1012 2-Me—C₆H₄ Me 1-Me-1H- 1 mp 111-112° C. tetrazol-5-yl1013 3-Me—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1014 4-Me—C₆H₄ Me 1-Me-1H- 1mp 138.5-139.5° C. tetrazol-5-yl 1015 2-Et—C₆H₄ Me 1-Me-1H- 1tetrazol-5-yl 1016 3-Et—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1017 4-Et—C₆H₄Me 1-Me-1H- 1 tetrazol-5-yl 1018 2-MeO—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl1019 3-MeO—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1020 4-MeO—C₆H₄ Me 1-Me-1H-1 tetrazol-5-yl 1021 2-CF₃—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 10223-CF₃—C₆H₄ Me 1-Me-1H- 1 ¹H-NMR(CDCl₃)δppm: tetrazol-5-yl 4.03(3H, s),4.21(3H, s), 4.99(2H, s), 6.82-7.53(8H, m) 1023 4-CF₃—C₆H₄ Me 1-Me-1H- 1tetrazol-5-yl 1024 2,4-F₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 10252,5-F₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 1026 2,6-F₂—C₆H₃ Me 1-Me-1H- 1tetrazol-5-yl 1027 3,4-F₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 10283,5-F₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 1029 2,3-Cl₂—C₆H₃ Me 1-Me-1H- 1tetrazol-5-yl 1030 2,4-Cl₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 10312,5-Cl₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 1032 3,4-Cl₂—C₆H₃ Me 1-Me-1H- 1mp 127-127.5° C. tetrazol-5-yl 1033 3,5-Cl₂—C₆H₃ Me 1-Me-1H- 1tetrazol-5-yl 1034 2,3-Me₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 10352,4-Me₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 1036 2,5-Me₂—C₆H₃ Me 1-Me-1H- 1mp 115.5-116.5° C. tetrazol-5-yl 1037 3,4-Me₂—C₆H₃ Me 1-Me-1H- 1tetrazol-5-yl 1038 3,5-Me₂—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 10392-Cl-4-Me—C₆H₃ Me 1-Me-1H- 1 tetrazol-5-yl 1040 2-Cl-5-Me—C₆H₃ Me1-Me-1H- 1 tetrazol-5-yl 1041 4-Cl-2-Me—C₆H₃ Me 1-Me-1H- 1 mp126.5-127.5° C. tetrazol-5-yl 1042 4-Cl-3-Me—C₆H₃ Me 1-Me-1H- 1tetrazol-5-yl 1043 3-Ph—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1044 4-Ph—C₆H₄Me 1-Me-1H- 1 mp 130.5-131.5° C. tetrazol-5-yl 1045 3-i-PrO—C₆H₄ Me1-Me-1H- 1 tetrazol-5-yl 1046 3-i-Pr—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl1047 4-i-Pr—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1048 3-t-Bu—C₆H₄ Me1-Me-1H- 1 tetrazol-5-yl 1049 2-MeS—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl1050 4-MeS—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1051 2,3,6-F₃—C₆H₂ Me1-Me-1H- 1 tetrazol-5-yl 1052 2,4,5-Cl₃—C₆H₂ Me 1-Me-1H- 1 tetrazol-5-yl1053 3-PhO—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1054 3,4,5-(MeO)₃— Me1-Me-1H- 1 C₆H₂ tetrazol-5-yl 1055 2,3,5-Me₃—C₆H₂ Me 1-Me-1H- 1tetrazol-5-yl 1056 3,4,5-Me₃—C₆H₂ Me 1-Me-1H- 1 tetrazol-5-yl 1057 C₆F₅Me 1-Me-1H- 1 tetrazol-5-yl 1058 4-Cl-3-Et—C₆H₃ Me 1-Me-1H- 1tetrazol-5-yl 1059 3-EtO—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 10604-EtO—C₆H₄ Me 1-Me-1H- 1 tetrazol-5-yl 1061 C₆H₅ Me 1-Me-1H- 0tetrazol-5-yl 1062 4-F—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 1063 3-Cl—C₆H₄Me 1-Me-1H- 0 tetrazol-5-yl 1064 4-Cl—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl1065 3-Me—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 1066 4-Me—C₆H₄ Me 1-Me-1H- 0tetrazol-5-yl 1067 4-Et—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 1068 4-NO₂—C₆H₄Me 1-Me-1H- 0 tetrazol-5-yl 1069 3,4-Cl₂—C₆H₃ Me 1-Me-1H- 0tetrazol-5-yl 1070 3,5-Cl₂—C₆H₃ Me 1-Me-1H- 0 tetrazol-5-yl 10713,4-Me₂—C₆H₃ Me 1-Me-1H- 0 tetrazol-5-yl 1072 3,5-Me₂—C₆H₃ Me 1-Me-1H- 0tetrazol-5-yl 1073 3-PhO—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 10744-Cl-3-Et—C₆H₃ Me 1-Me-1H- 0 tetrazol-5-yl 1075 3-EtO—C₆H₄ Me 1-Me-1H- 0tetrazol-5-yl 1076 3-CF₃—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 10774-CF₃—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 1078 3-i-PrO—C₆H₄ Me 1-Me-1H- 0tetrazol-5-yl 1079 3-i-Pr—C₆H₄ Me 1-Me-1H- 0 tetrazol-5-yl 10804-Cl-3-Me—C₆H₃ Me 1-Me-1H- 0 tetrazol-5-yl 1081 Pyridin-2-yl Me 1-Me-1H-1 tetrazol-5-yl 1082 Pyridin-3-yl Me 1-Me-1H- 1 tetrazol-5-yl 1083 5-Cl-Me 1-Me-1H- 1 pyridin-2-yl tetrazol-5-yl 1084 3-Cl- Me 1-Me-1H- 1pyridin-2-yl tetrazol-5-yl 1085 6-Cl- Me 1-Me-1H- 1 pyridin-2-yltetrazol-5-yl 1086 2-Cl- Me 1-Me-1H- 1 pyridin-3-yl tetrazol-5-yl 10875-CF₃- Me 1-Me-1H- 1 pyridin-2-yl tetrazol-5-yl 1088 3-CF₃- Me 1-Me-1H-1 pyridin-2-yl tetrazol-5-yl 1089 6-CF₃-3-Cl- Me 1-Me-1H- 1 pyridin-2-yltetrazol-5-yl 1090 5-CF₃-3-Cl- Me 1-Me-1H- 1 pyridin-2-yl tetrazol-5-yl1091 Benzothiazol- Me 1-Me-1H- 1 2-yl tetrazol-5-yl 1092 Benzothiazol-Me 1-Me-1H- 1 2-yl tetrazol-5-yl 1093 Quinolin-2-yl Me 1-Me-1H- 1tetrazol-5-yl 1094 5-CF₃-1,3,4- Me 1-Me-1H- 1 thiadiazol-2-yltetrazol-5-yl 1095 Pyrimidin-2-yl Me 1-Me-1H- 1 tetrazol-5-yl 10965-Cl-6-Me- Me 1-Me-1H- 1 pyrimidin-4-yl tetrazol-5-yl 1097 5-Et-6-Me- Me1-Me-1H- 1 pyrimidin-4-yl tetrazol-5-yl 1098 6-Cl- Me 1-Me-1H- 1pyrazin-2-yl tetrazol-5-yl 1099 3,6-Me₂- Me 1-Me-1H- 1 pyrazin-2-yltetrazol-5-yl 1100 5-Me- Me 1-Me-1H- 1 isoxazol-3-yl tetrazol-5-yl 1101C₆H₅ Me 1-Me-2- 1 ¹H-NMR-(CDCl₃)δppm: 2.75(3H, s), imidazolin-2-yl3.40(2H, t, J=9.8), 3.92(2H, t, J=9.8), 3.97(3H, s), 5.37(2H, s),6.93-6.98(3H, m), 7.25-7.35(3H, m), 7.40(1H, t, J=7.5), 7.52(1H, d,J=7.5), 7.68(1H, d, J=7.5) 1102 2-F—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl1103 3-F—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1104 4-F—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1105 2-Cl—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11063-Cl—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1107 4-Cl—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1108 2-Br—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11093-Br—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1110 4-Br—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1111 3-I—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11122-Me—C₆H₄ Me 1-Me-2- 1 ¹H-NMR(CDCl₃)δppm: 2.33(3H, s), imidazolin-2-yl2.74(3H, s), 3.40(2H, t, J=9.8), 3.93(2H, t, J=9.8), 4.02(3H, s),5.38(2H, s), 6.82- 6.88(2H, m), 7.31-7.35(2H, m), 7.33(1H, t, J=7.7),7.41(1H, t, J=7.7), 7.51(1H, d, J=7.7), 7.76(1H, d, J=7.7) 11133-Me—C₆H₄ Me 1-Me-2- 1 ¹H-NMR(CDCl₃)δppm: 2.32(3H, s), imidazolin-2-yl2.75(3H, s), 3.40(2H, t, J=9.8), 3.92(2H, t, J=9.8), 3.90(3H, s),5.35(2H, s), 6.75- 6.80(3H, m), 7.16(1H, t, J=7.6), 7.30- 7.43(2H, m),7.51(1H, dd, J=7.6), 1.5), 7.68(1H, d, J=7.6) 1114 4-Me—C₆H₄ Me 1-Me-2-1 ¹H-NMR(CDCl₃)δppm: 2.28(3H, s) imidazolin-2-yl 2.75(3H, s), 3.40(2H,t, J=9.8), 3.92(2H, t, J=9.8), 3.98(3H, s), 5.34(2H, s), 6.85(2H, d,J=8.5), 7.07(2H, d, J=8.5), 7.29-7.42(2H, m), 7.51(1H, dd, J=7.6, 1.5),7.67(1H, d, J=7.6) 1115 2-Et—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11163-Et—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1117 4-Et—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1118 2-MeO—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11193-MeO—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1120 4-MeO—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1121 2-CF₃—C₆H₄ Me 1-Me-2- 1 ¹H-NMR(CDCl₃)δppm: 2.75(3H,s), imidazolin-2-yl 3.41(2H, t, J=9.8), 3.93(2H, t, J=9.8), 4.02(3H, s),5.47(2H, s), 6.86-6.93(2H, m), 7.18(1H, ddd, J=8.5, 7.6, 1.5), 7.31-7.45(3H, m), 7.49(1H, dd, J=7.6, 1.5), 7.81(1H, d, J=7.6) 11223-CF₃—C₆H₄ Me 1-Me-2- 1 Isomer A ¹H-NMR(CDCl₃)δppm: imidazolin-2-yl2.75(3H, s), 3.41(2H, t, J=9.8), 3.92(t, J=9.8), 3.97(3H, s), 5.35(2H,s), 6.84-6.99(3H, m), 7.19(1H, t, J=8.0), 7.32-7.44(2H, m), 7.51(1H, dd,J=7.3, 1.4), 7.64(1H, d, J=7.0) Isomer B ¹H-NMR(CDCl₃)δppm: 3.03(3H, s),3.38(2H, t, J=9.9), 3.77(2H, t, J=9.9), 3.97(3H, s), 4.99(2H, s),6.83-7.16(4H, m), 7.23(1H, d, J=7.6), 7.34-7.39(2H, m), 7.49(1H, d,J=6.4) 1123 4-CF₃—C₆H₄ Me 1-Me-2- 1 mp 53-56° C. imidazolin-2-yl 11242,4-F₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 1125 2,5-F₂—C₆H₃ Me 1-Me-2- 1imidazolin-2-yl 1126 2,6-F₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 11273,4-F₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 1128 3,5-F₂—C₆H₃ Me 1-Me-2- 1imidazolin-2-yl 1129 2,3-Cl₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 11302,4-Cl₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 1131 2,5-Cl₂—C₆H₃ Me 1-Me-2- 1imidazolin-2-yl 1132 3,4-Cl₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 11333,5-Cl₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 1134 2,3-Me₂—C₆H₃ Me 1-Me-2- 1imidazolin-2-yl 1135 2,4-Me₂—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 11362,5-Me₂—C₆H₃ Me 1-Me-2- 1 mp 88-90° C. imidazolin-2-yl 1137 3,4-Me₂—C₆H₃Me 1-Me-2- 1 imidazolin-2-yl 1138 3,5-Me₂—C₆H₃ Me 1-Me-2- 1imidazolin-2-yl 1139 2-Cl-4-Me—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 11402-Cl-5-Me—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 1141 4-Cl-2-Me—C₆H₃ Me1-Me-2- 1 imidazolin-2-yl 1142 4-Cl-3-Me—C₆H₃ Me 1-Me-2- 1imidazolin-2-yl 1143 3-Ph—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11444-Ph—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1145 3-i-PrO—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1146 3-i-Pr—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11474-i-Pr—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1148 3-t-Bu—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1149 2-MeS—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 11504-MeS—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1151 2,3,6-F₃—C₆H₂ Me 1-Me-2- 1imidazolin-2-yl 1152 2,4,5-Cl₃—C₆H₂ Me 1-Me-2- 1 imidazolin-2-yl 11533-PhO—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1154 3,4,5-(MeO)₃— Me 1-Me-2- 1C₆H₂ imidazolin-2-yl 1155 2,3,5-Me₃—C₆H₂ Me 1-Me-2- 1 imidazolin-2-yl1156 3,4,5-Me₃—C₆H₂ Me 1-Me-2- 1 imidazolin-2-yl 1157 C₆F₅ Me 1-Me-2- 1imidazolin-2-yl 1158 4-Cl-3-Et—C₆H₃ Me 1-Me-2- 1 imidazolin-2-yl 11593-EtO—C₆H₄ Me 1-Me-2- 1 imidazolin-2-yl 1160 4-EtO—C₆H₄ Me 1-Me-2- 1imidazolin-2-yl 1161 C₆H₅ Me 1-Me-2- 0 ¹H-NMR(CDCl₃)δppm:imidazolin-2-yl 2.80(2.91)(3H, s), 3.03(3.14)(2H, s), 3.53(3.61)(2H, t,J=9.8), 4.05(3.95)(3H, s), 6.96- 7.72(9H, m) 1162 4-F—C₆H₄ Me 1-Me-2- 0imidazolin-2-yl 1163 3-Cl—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 11644-Cl—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 1165 3-Me—C₆H₄ Me 1-Me-2- 0imidazolin-2-yl 1166 4-Me—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 11674-Et—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 1168 4-NO₂—C₆H₄ Me 1-Me-2- 0imidazolin-2-yl 1169 3,4-Cl₂—C₆H₃ Me 1-Me-2- 0 imidazolin-2-yl 11703,5-Cl₂—C₆H₃ Me 1-Me-2- 0 imidazolin-2-yl 1171 3,4-Me₂—C₆H₃ Me 1-Me-2- 0imidazolin-2-yl 1172 3,5-Me₂—C₆H₃ Me 1-Me-2- 0 imidazolin-2-yl 11733-PhO—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 1174 4-Cl-3-Et—C₆H₃ Me 1-Me-2- 0imidazolin-2-yl 1175 3-EtO—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 11763-CF₃—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 1177 4-CF₃—C₆H₄ Me 1-Me-2- 0imidazolin-2-yl 1178 3-i-PrO—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 11793-i-Pr—C₆H₄ Me 1-Me-2- 0 imidazolin-2-yl 1180 4-Cl-3-Me—C₆H₃ Me 1-Me-2-0 imidazolin-2-yl 1181 Pyridin-2-yl Me 1-Me-2- 1 imidazolin-2-yl 1182Pyridin-3-yl Me 1-Me-2- 1 imidazolin-2-yl 1183 5-Cl- Me 1-Me-2- 1pyridin-2-yl imidazolin-2-yl 1184 3-Cl- Me 1-Me-2- 1 pyridin-2-ylimidazolin-2-yl 1185 6-Cl- Me 1-Me-2- 1 pyridin-2-yl imidazolin-2-yl1186 2-Cl- Me 1-Me-2- 1 pyridin-3-yl imidazolin-2-yl 1187 5-CF₃- Me1-Me-2- 1 pyridin-2-yl imidazolin-2-yl 1188 3-CF₃- Me 1-Me-2- 1pyridin-2-yl imidazolin-2-yl 1189 6-CF₃-3-Cl- Me 1-Me-2- 1 pyridin-2-ylimidazolin-2-yl 1190 5-CF₃-3-Cl- Me 1-Me-2- 1 pyridin-2-ylimidazolin-2-yl 1191 Benzothiazol- Me 1-Me-2- 1 2-yl imidazolin-2-yl1192 Benzothiazol- Me 1-Me-2- 1 2-yl imidazolin-2-yl 1193 Quinolin-2-ylMe 1-Me-2- 1 imidazolin-2-yl 1194 5-CF₃-1,3,4- Me 1-Me-2- 1thiadiazol-2-yl imidazolin-2-yl 1195 Pyrimidin-2-yl Me 1-Me-2- 1imidazolin-2-yl 1196 5-Cl-6-Me- Me 1-Me-2- 1 pyrimidin-4-ylimidazolin-2-yl 1197 5-Et-6-Me- Me 1-Me-2- 1 pyrimidin-4-ylimidazolin-2-yl 1198 6-Cl- Me 1-Me-2- 1 pyrazin-2-yl imidazolin-2-yl1199 3,6-Me₂- Me 1-Me-2- 1 pyrazin-2-yl imidazolin-2-yl 1200 5-Me- Me1-Me-2- 1 isoxazol-3-yl imidazolin-2-yl 1201 C₆H₅ Me 2-Isoxazolin-3-yl 11202 2-F—C₆H₄ Me 2-Isoxazolin-3-yl 1 1203 3-F—C₆H₄ Me 2-Isoxazolin-3-yl1 1204 4-F—C₆H₄ Me 2-Isoxazolin-3-yl 1 1205 2-Cl—C₆H₄ Me2-Isoxazolin-3-yl 1 1206 3-Cl—C₆H₄ Me 2-Isoxazolin-3-yl 1 1207 4-Cl—C₆H₄Me 2-Isoxazolin-3-yl 1 1208 2-Br—C₆H₄ Me 2-Isoxazolin-3-yl 1 12093-Br—C₆H₄ Me 2-Isoxazolin-3-yl 1 1210 4-Br—C₆H₄ Me 2-Isoxazolin-3-yl 11211 3-I—C₆H₄ Me 2-Isoxazolin-3-yl 1 1212 2-Me—C₆H₄ Me 2-Isoxazolin-3-yl1 1213 3-Me—C₆H₄ Me 2-Isoxazolin-3-yl 1 1214 4-Me—C₆H₄ Me2-Isoxazolin-3-yl 1 1215 2-Et—C₆H₄ Me 2-Isoxazolin-3-yl 1 1216 3-Et—C₆H₄Me 2-Isoxazolin-3-yl 1 1217 4-Et—C₆H₄ Me 2-Isoxazolin-3-yl 1 12182-MeO—C₆H₄ Me 2-Isoxazolin-3-yl 1 1219 3-MeO—C₆H₄ Me 2-Isoxazolin-3-yl 11220 4-MeO—C₆H₄ Me 2-Isoxazolin-3-yl 1 1221 2-CF₃—C₆H₄ Me2-Isoxazolin-3-yl 1 1222 3-CF₃—C₆H₄ Me 2-Isoxazolin-3-yl 1 12234-CF₃—C₆H₄ Me 2-Isoxazolin-3-yl 1 1224 2,4-F₂—C₆H₃ Me 2-Isoxazolin-3-yl1 1225 2,5-F₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 1226 2,6-F₂—C₆H₃ Me2-Isoxazolin-3-yl 1 1227 3,4-F₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 12283,5-F₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 1229 2,3-Cl₂—C₆H₃ Me2-Isoxazolin-3-yl 1 1230 2,4-Cl₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 12312,5-Cl₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 1232 3,4-Cl₂—C₆H₃ Me2-Isoxazolin-3-yl 1 1233 3,5-Cl₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 12342,3-Me₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 1235 2,4-Me₂—C₆H₃ Me2-Isoxazolin-3-yl 1 1236 2,5-Me₂—C₆H₃ Me 2-Isoxazolin-3-yl 12.17-2.29(6H, m), 3.24- 3.38(2H, m), 3.95(4.00)(3H, s), 4.28(4.44)(2H,t, J=10.4), 4.93-5.06(2H, m), 6.59- 7.58(7H, m) 1237 3,4-Me₂—C₆H₃ Me2-Isoxazolin-3-yl 1 1238 3,5-Me₂—C₆H₃ Me 2-Isoxazolin-3-yl 1 12392-Cl-4-Me—C₆H₃ Me 2-Isoxazolin-3-yl 1 1240 2-Cl-5-Me—C₆H₃ Me2-Isoxazolin-3-yl 1 1241 4-Cl-2-Me—C₆H₃ Me 2-Isoxazolin-3-yl 1 12424-Cl-3-Me—C₆H₃ Me 2-Isoxazolin-3-yl 1 1243 3-Ph—C₆H₄ Me2-Isoxazolin-3-yl 1 1244 4-Ph—C₆H₄ Me 2-Isoxazolin-3-yl 1 12453-i-PrO—C₆H₄ Me 2-Isoxazolin-3-yl 1 1246 3-i-Pr—C₆H₄ Me2-Isoxazolin-3-yl 1 1247 4-i-Pr—C₆H₄ Me 2-Isoxazolin-3-yl 1 12483-t-Bu—C₆H₄ Me 2-Isoxazolin-3-yl 1 1249 2-MeS—C₆H₄ Me 2-Isoxazolin-3-yl1 1250 4-MeS—C₆H₄ Me 2-Isoxazolin-3-yl 1 1251 2,3,6-F₃—C₆H₂ Me2-Isoxazolin-3-yl 1 1252 2,4,5-Cl₃—C₆H₂ Me 2-Isoxazolin-3-yl 1 12533-PhO—C₆H₄ Me 2-Isoxazolin-3-yl 1 1254 3,4,5-(MeO)₃—C₆H₂ Me2-Isoxazolin-3-yl 1 1255 2,3,5-Me₃—C₆H₂ Me 2-Isoxazolin-3-yl 1 12563,4,5-Me₃—C₆H₂ Me 2-Isoxazolin-3-yl 1 1257 C₆F₅ Me 2-Isoxazolin-3-yl 11258 4-Cl₃—Et—C₆H₃ Me 2-Isoxazolin-3-yl 1 1259 3-EtO—C₆H₄ Me2-Isoxazolin-3-yl 1 1260 4-EtO—C₆H₄ Me 2-Isoxazolin-3-yl 1 1261 C₆H₅ Me2-Isoxazolin-3-yl 0 1262 4-F—C₆H₄ Me 2-Isoxazolin-3-yl 0 1263 3-Cl—C₆H₄Me 2-Isoxazolin-3-yl 0 1264 4-Cl—C₆H₄ Me 2-Isoxazolin-3-yl 0 12653-Me—C₆H₄ Me 2-Isoxazolin-3-yl 0 1266 4-Me—C₆H₄ Me 2-Isoxazolin-3-yl 01267 4-Et—C₆H₄ Me 2-Isoxazolin-3-yl 0 1268 4-NO₂—C₆H₄ Me2-Isoxazolin-3-yl 0 1269 3,4-Cl₂—C₆H₃ Me 2-Isoxazolin-3-yl 0 12703,5-Cl₂—C₆H₃ Me 2-Isoxazolin-3-yl 0 1271 3,4-Me₂—C₆H₃ Me2-Isoxazolin-3-yl 0 1272 3,5-Me₂—C₆H₃ Me 2-Isoxazolin-3-yl 0 12733-PhO—C₆H₄ Me 2-Isoxazolin-3-yl 0 1274 4-Cl-3-Et—C₆H₃ Me2-Isoxazolin-3-yl 0 1275 3-EtO—C₆H₄ Me 2-Isoxazolin-3-yl 0 12763-CF₃—C₆H₄ Me 2-Isoxazolin-3-yl 0 1277 4-CF₃—C₆H₄ Me 2-Isoxazolin-3-yl 01278 3-i-PrO—C₆H₄ Me 2-Isoxazolin-3-yl 0 1279 3-i-Pr—C₆H₄ Me2-Isoxazolin-3-yl 0 1280 4-Cl-3-Me—C₆H₃ Me 2-Isoxazolin-3-yl 0 1281Pyridin-2-yl Me 2-Isoxazolin-3-yl 1 1282 Pyridin-3-yl Me2-Isoxazolin-3-yl 1 1283 5-Cl- Me 2-Isoxazolin-3-yl 1 pyridin-2-yl 12843-Cl- Me 2-Isoxazolin-3-yl 1 pyridin-2-yl 1285 6-Cl- Me2-Isoxazolin-3-yl 1 pyridin-2-yl 1286 2-Cl- Me 2-Isoxazolin-3-yl 1pyridin-2-yl 1287 5-CF₃- Me 2-Isoxazolin-3-yl 1 pyridin-2-yl 1288 3-CF₃-Me 2-Isoxazolin-3-yl 1 pyridin-2-yl 1289 6-CF₃-3-Cl- Me2-Isoxazolin-3-yl 1 pyridin-2-yl 1290 5-CF₃-3-Cl- Me 2-Isoxazolin-3-yl 1pyridin-2-yl 1291 Benzothiazol-2-yl Me 2-Isoxazolin-3-yl 1 1292Benzoxazol-2-yl Me 2-Isoxazolin-3-yl 1 1293 Quinolin-2-yl Me2-Isoxazolin-3-yl 1 1294 5-CF₃-1,3,4- Me 2-Isoxazolin-3-yl 1thiadiazol-2-yl 1295 Pyrimidin-2-yl Me 2-Isoxazolin-3-yl 1 12965-Cl-6-Me- Me 2-Isoxazolin-3-yl 1 pyrimidin-4-yl 1297 5-Et-6-Me- Me2-Isoxazolin-3-yl 1 pyrimidin-4-yl 1298 6-Cl- Me 2-Isoxazolin-3-yl 1pyrazin-2-yl 1299 3,6-Me₂- Me 2-Isoxazolin-3-yl 1 pyrazin-2-yl 13005-Me- Me 2-Isoxazolin-3-yl 1 isoxazol-3-yl 1301 C₆H₅ Me 2-Oxazolin-2-yl1 mp 69-70° C. 1302 2-F—C₆H₄ Me 2-Oxazolin-2-yl 1 1303 3-F—C₆H₄ Me2-Oxazolin-2-yl 1 1304 4-F—C₆H₄ Me 2-Oxazolin-2-yl 1 1305 2-Cl—C₆H₄ Me2-Oxazolin-2-yl 1 mp 89-90° C. 1306 3-Cl—C₆H₄ Me 2-Oxazolin-2-yl 1 mp82-83° C. 1307 4-Cl—C₆H₄ Me 2-Oxazolin-2-yl 1 mp 76-80° C. 13083-Br—C₆H₄ Me 2-Oxazolin-2-yl 1 1309 4-Br—C₆H₄ Me 2-Oxazolin-2-yl 1 13102-Me—C₆H₄ Me 2-Oxazolin-2-yl 1 ¹H-NMR(CDCl₃)δppm: 2.30(3H, s), 4.02(2H,t, J=9.8), 4.05(3H, s), 4.32(2H, t, J=9.8), 5.25(2H, s), 6.82(1H, d,J=8.3), 6.86(1H, t, J=7.6), 7.10-7.16(2H, m), 7.35(1H, t, J=7.6),7.41-7.48(2H, m), 7.68(1H, d, J=7.6) 1311 3-Me—C₆H₄ Me 2-Oxazolin-2-yl 1¹H-NMR(CDCl₃)δppm: 2.31(3H, s), 4.00(2H, t, J=9.8), 4.03(3H, s),4.32(2H, t, J=9.8), 5.21(2H, s), 6.72-6.78(3H, m), 7.14(1H, t, J=7.6),7.31- 7.48(3H, m), 7.62(1H, d, J=7.6) 1312 4-Me—C₆H₄ Me 2-Oxazolin-2-yl1 ¹H-NMR(CDCl₃)δppm: 2.27(3H, s), 4.00(2H, t, J=9.6), 4.03(3H, s),4.31(2H, t, J=9.6), 5.20(2H, s), 6.84(2H, d, J=8.6), 7.06(2H, d, J=8.6),7.31-7.47(3H, m), 7.62(1H, d, J=7.6) 1313 3-Et—C₆H₄ Me 2-Oxazolin-2-yl 11314 2-MeO—C₆H₄ Me 2-Oxazolin-2-yl 1 1315 3-MeO—C₆H₄ Me 2-Oxazolin-2-yl1 1316 4-MeO—C₆H₄ Me 2-Oxazolin-2-yl 1 1317 4-Et—C₆H₄ Me 2-Oxazolin-2-yl1 1318 3-CF₃—C₆H₄ Me 2-Oxazolin-2-yl 1 1319 4-CF₃—C₆H₄ Me2-Oxazolin-2-yl 1 1320 3,5-F₂—C₆H₃ Me 2-Oxazolin-2-yl 1 13212,3-Cl₂—C₆H₃ Me 2-Oxazolin-2-yl 1 1322 2,4-Cl₂—C₆H₃ Me 2-Oxazolin-2-yl 11323 2,5-Cl₂—C₆H₃ Me 2-Oxazolin-2-yl 1 1324 3,4-Cl₂—C₆H₃ Me2-Oxazolin-2-yl 1 1325 3,5-Cl₃—C₆H₃ Me 2-Oxazolin-2-yl 1 13262,3-Me₂—C₆H₃ Me 2-Oxazolin-2-yl 1 1327 2,4-Me₂—C₆H₃ Me 2-Oxazolin-2-yl 11328 2,5-Me₂—C₆H₃ Me 2-Oxazolin-2-yl 1 mp 81-85° C. 1329 3,4-Me₂—C₆H₃ Me2-Oxazolin-2-yl 1 1330 2-Cl-4-Me—C₆H₃ Me 2-Oxazolin-2-yl 1 13312-Cl-5-Me—C₆H₃ Me 2-Oxazolin-2-yl 1 1332 4-Cl-3-Me—C₆H₃ Me2-Oxazolin-2-yl 1 1333 3-Ph—C₆H₄ Me 2-Oxazolin-2-yl 1 1334 3-i-PrO—C₆H₄Me 2-Oxazolin-2-yl 1 1335 3-PhO—C₆H₄ Me 2-Oxazolin-2-yl 1 13364-Cl-2-Me—C₆H₃ Me 2-Oxazolin-2-yl 1 1337 4-Cl-3-Et—C₆H₃ Me2-Oxazolin-2-yl 1 1338 3-EtO—C₆H₄ Me 2-Oxazolin-2-yl 1 13392-Cl-4-Me—C₆H₃ Me 2-Oxazolin-2-yl 1 1340 2,4,5-Cl₃—C₆H₂ Me2-Oxazolin-2-yl 1 1341 C₆H₅ Me 2-Oxazolin-2-yl 0 Isomer A:¹H-NMR(CDCl₃)δ ppm: 3.63(2H, t, J=9.8), 4.08(308(2H, t, J=9.8), 6.94-7.40(8H, m), 7.69(1H, dd, J=7.9, 1.9) Isomer B: ¹H-NMR(CDCl₃)δ ppm:3.91(2H, t, J=9.8), 3.96(3H, s), 4.37(2H, t, J=9.8), 6.91-7.37(9H, m)1342 4-F—C₆H₄ Me 2-Oxazolin-2-yl 0 1343 3-Cl—C₆H₄ Me 2-Oxazolin-2-yl 01344 4-Cl—C₆H₄ Me 2-Oxazolin-2-yl 0 1345 4-Me—C₆H₄ Me 2-Oxazolin-2-yl 01346 3,5-Cl₂—C₆H₃ Me 2-Oxazolin-2-yl 0 1347 3,4-Me₂—C₆H₃ Me2-Oxazolin-2-yl 0 1348 2-Cl- Me 2-Oxazolin-2-yl 1 pyridin-3-yl 13495-CF₃- Me 2-Oxazolin-2-yl 1 pyridin-2-yl 1350 5-Cl- Me 2-Oxazolin-2-yl 1pyridin-2-yl 1351 C₆H₅ Me 5-Me-2-isoxazolin- 1 3-yl 1352 2-F—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1353 3-F—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1354 4-F—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1355 2-Cl—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1356 3-Cl—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1357 4-Cl—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1358 3-Br—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1359 4-Br—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1360 2-Me—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1361 3-Me—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1362 4-Me—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1363 3-Et—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1364 2-MeO—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1365 3-MeO—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1366 4-MeO—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1367 4-Et—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1368 3-CF₃—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1369 4-CF₃—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1370 3,5-F₂—C₆H₃ Me5-Me-2-isoxazolin- 1 3-yl 1371 2,3-Cl₂—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl1372 2,4-Cl₂—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl 1373 2,5-Cl₂—C₆H₃ Me5-Me-2-isoxazolin- 1 3-yl 1374 3,4-Cl₂—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl1375 3,5-Cl₃—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl 1376 2,3-Me₂—C₆H₃ Me5-Me-2-isoxazolin- 1 3-yl 1377 2,4-Me₂—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl1378 2,5-Me₂—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl 1379 3,4-Me₂—C₆H₃ Me5-Me-2-isoxazolin- 1 3-yl 1380 2-Cl-4-Me—C₆H₃ Me 5-Me-2-isoxazolin- 13-yl 1381 2-Cl-5-Me—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl 13824-Cl-3-Me—C₆H₃ Me 5-Me-2-isoxazolin- 1 3-yl 1383 3-Ph—C₆H₄ Me5-Me-2-isoxazolin- 1 3-yl 1384 3-i-PrO—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl1385 3-PhO—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1386 4-Cl-2-Me—C₆H₃ Me5-Me-2-isoxazolin- 1 3-yl 1387 4-Cl-3-Et—C₆H₃ Me 5-Me-2-isoxazolin- 13-yl 1388 3-EtO—C₆H₄ Me 5-Me-2-isoxazolin- 1 3-yl 1389 2-Cl-4-Me—C₆H₃ Me5-Me-2-isoxazolin- 1 3-yl 1390 2,4,5-Cl₃—C₆H₂ Me 5-Me-2-isoxazolin- 13-yl 1391 C₆H₅ Me 5-Me-2-isoxazolin- 0 3-yl 1392 4-F—C₆H₄ Me5-Me-2-isoxazolin- 0 3-yl 1393 3-Cl—C₆H₄ Me 5-Me-2-isoxazolin- 0 3-yl1394 4-Cl—C₆H₄ Me 5-Me-2-isoxazolin- 0 3-yl 1395 4-Me—C₆H₄ Me5-Me-2-isoxazolin- 0 3-yl 1396 3,5-Cl₂—C₆H₃ Me 5-Me-2-isoxazolin- 0 3-yl1397 3,4-Me₂—C₆H₃ Me 5-Me-2-isoxazolin- 0 3-yl 1398 2-Cl- Me5-Me-2-isoxazolin- 1 pyridin-2-yl 3-yl 1399 5-CF₃- Me 2-Oxazolin-2-yl 1pyridin-2-yl 3-yl 1400 5-Cl- Me 5-Me-2-isoxazolin- 1 pyridin-2-yl 3-yl1401 C₆H₅ Me Imidazol-2-yl 1 1402 2-F—C₆H₄ Me Imidazol-2-yl 1 14033-F—C₆H₄ Me Imidazol-2-yl 1 1404 4-F—C₆H₄ Me Imidazol-2-yl 1 14052-Cl—C₆H₄ Me Imidazol-2-yl 1 1406 3-Cl—C₆H₄ Me Imidazol-2-yl 1 14074-Cl—C₆H₄ Me Imidazol-2-yl 1 1408 3-Br—C₆H₄ Me Imidazol-2-yl 1 14094-Br—C₆H₄ Me Imidazol-2-yl 1 1410 2-Me—C₆H₄ Me Imidazol-2-yl 1 14113-Me—C₆H₄ Me Imidazol-2-yl 1 1412 4-Me—C₆H₄ Me Imidazol-2-yl 1 14133-Et—C₆H₄ Me Imidazol-2-yl 1 1414 2-MeO—C₆H₄ Me Imidazol-2-yl 1 14153-MeO—C₆H₄ Me Imidazol-2-yl 1 1416 4-MeO—C₆H₄ Me Imidazol-2-yl 1 14174-Et—C₆H₄ Me Imidazol-2-yl 1 1418 3-CF₃—C₆H₄ Me Imidazol-2-yl 1 14194-CF₃—C₆H₄ Me Imidazol-2-yl 1 1420 3,5-F₂—C₆H₃ Me Imidazol-2-yl 1 14212,3-Cl₂—C₆H₃ Me Imidazol-2-yl 1 1422 2,4-Cl₂—C₆H₃ Me Imidazol-2-yl 11423 2,5-Cl₂—C₆H₃ Me Imidazol-2-yl 1 1424 3,4-Cl₂—C₆H₃ Me Imidazol-2-yl1 1425 3,5-Cl₃—C₆H₃ Me Imidazol-2-yl 1 1426 2,3-Me₂—C₆H₃ MeImidazol-2-yl 1 1427 2,4-Me₂—C₆H₃ Me Imidazol-2-yl 1 1428 2,5-Me₂—C₆H₃Me Imidazol-2-yl 1 mp 153-154° C. 1429 3,4-Me₂—C₆H₃ Me Imidazol-2-yl 11430 2-Cl-4-Me—C₆H₃ Me Imidazol-2-yl 1 1431 2-Cl-5-Me—C₆H₃ MeImidazol-2-yl 1 1432 4-Cl-3-Me—C₆H₃ Me Imidazol-2-yl 1 1433 3-Ph—C₆H₄ MeImidazol-2-yl 1 1434 3-i-PrO—C₆H₄ Me Imidazol-2-yl 1 1435 3-PhO—C₆H₄ MeImidazol-2-yl 1 1436 4-Cl-2-Me—C₆H₃ Me Imidazol-2-yl 1 14374-Cl-3-Et—C₆H₃ Me Imidazol-2-yl 1 1438 3-EtO—C₆H₄ Me Imidazol-2-yl 11439 2-Cl-4-Me—C₆H₃ Me Imidazol-2-yl 1 1440 2,4,5-Cl₃—C₆H₂ MeImidazol-2-yl 1 1441 C₆H₅ Me Imidazol-2-yl 0 1442 4-F—C₆H₄ MeImidazol-2-yl 0 1443 3-Cl—C₆H₄ Me Imidazol-2-yl 0 1444 4-Cl—C₆H₄ MeImidazol-2-yl 0 1445 4-Me—C₆H₄ Me Imidazol-2-yl 0 1446 3,5-Cl₂—C₆H₃ MeImidazol-2-yl 0 1447 3,4-Me₂—C₆H₃ Me Imidazol-2-yl 0 1448 2-Cl- MeImidazol-2-yl 1 pyridin-3-yl 1449 5-CF₃- Me Imidazol-2-yl 1 pyridin-2-yl1450 5-Cl- Me Imidazol-2-yl 1 pyridin-2-yl 1451 C₆H₅ Me2-Imidazolin-2-yl 1 mp 91-92° C. 1452 2-F—C₆H₄ Me 2-Imidazolin-2-yl 11453 3-F—C₆H₄ Me 2-Imidazolin-2-yl 1 1454 4-F—C₆H₄ Me 2-Imidazolin-2-yl1 1455 2-Cl—C₆H₄ Me 2-Imidazolin-2-yl 1 mp 121-123° C. 1456 3-Cl—C₆H₄ Me2-Imidazolin-2-yl 1 ¹H-NMR(CDCl₃)δppm: 3.67(4H, brs), 3.95(4.02)(3H, s),4.97(5.11)(2H, s), 6.78- 6.81(1H, m), 6.90-6.95(2H, m), 7.13-7.23(2H,m), 7.35- 7.41(2H, m), 7.49-7.51(1H, m) 1457 4-Cl—C₆H₄ Me2-Imidazolin-2-yl 1 mp 113-114° C. 1458 3-Br—C₆H₄ Me 2-Imidazolin-2-yl 11459 4-Br—C₆H₄ Me 2-Imidazolin-2-yl 1 1460 2-Me—C₆H₄ Me2-Imidazolin-2-yl 1 mp 96-100° C. 1461 3-Me—C₆H₄ Me 2-Imidazolin-2-yl 1¹H-NMR(CDCl₃δppm: 2.31(2.27)(3H, s), 3.66(4H, brs), 4.02(3.94)(3H, s),5.11(4.95)(2H, s), 6.54- 6.76(3H, m), 7.04-7.15(1H, m), 7.21-7.41(3H,m), 7.50- 7.53(1H, m) 1462 4-Me—C₆H₄ Me 2-Imidazolin-2-yl 1 mp 89-90° C.1463 3-Et—C₆H₄ Me 2-Imidazolin-2-yl 1 1464 2-MeO—C₆H₄ Me2-Imidazolin-2-yl 1 1465 3-MeO—C₆H₄ Me 2-Imidazolin-2-yl 1 14664-MeO—C₆H₄ Me 2-Imidazolin-2-yl 1 1467 4-Et—C₆H₄ Me 2-Imidazolin-2-yl 11468 3-CF₃—C₆H₄ Me 2-Imidazolin-2-yl 1 1469 4-CF₃—C₆H₄ Me2-Imidazolin-2-yl 1 1470 3,5-F₂—C₆H₃ Me 2-Imidazolin-2-yl 1 14712,3-Cl₂—C₆H₃ Me 2-Imidazolin-2-yl 1 1472 2,4-Cl₂—C₆H₃ Me2-Imidazolin-2-yl 1 1473 2,5-Cl₂—C₆H₃ Me 2-Imidazolin-2-yl 1 14743,4-Cl₂—C₆H₃ Me 2-Imidazolin-2-yl 1 1475 3,5-Cl₃—C₆H₃ Me2-Imidazolin-2-yl 1 1476 2,3-Me₂—C₆H₃ Me 2-Imidazolin-2-yl 1 14772,4-Me₂—C₆H₃ Me 2-Imidazolin-2-yl 1 1478 2,5-Me₂—C₆H₃ Me2-Imidazolin-2-yl 1 mp 97-101° C. 1479 3,4-Me₂—C₆H₃ Me 2-Imidazolin-2-yl1 1480 2-Cl-4-Me—C₆H₃ Me 2-Imidazolin-2-yl 1 1481 2-Cl-5-Me—C₆H₃ Me2-Imidazolin-2-yl 1 1482 4-Cl-3-Me—C₆H₃ Me 2-Imidazolin-2-yl 1 14833-Ph—C₆H₄ Me 2-Imidazolin-2-yl 1 1484 3-i-PrO—C₆H₄ Me 2-Imidazolin-2-yl1 1485 3-PhO—C₆H₄ Me 2-Imidazolin-2-yl 1 1486 4-Cl-2-Me—C₆H₃ Me2-Imidazolin-2-yl 1 1487 4-Cl-3-Et—C₆H₃ Me 2-Imidazolin-2-yl 1 14883-EtO—C₆H₄ Me 2-Imidazolin-2-yl 1 1489 2-Cl-4-Me—C₆H₃ Me2-Imidazolin-2-yl 1 1490 2,4,5-Cl₃—C₆H₂ Me 2-Imidazolin-2-yl 1 1491 C₆H₅Me 2-Imidazolin-2-yl 0 mp 95-99° C. 1492 4-F—C₆H₄ Me 2-Imidazolin-2-yl 01493 3-Cl—C₆H₄ Me 2-Imidazolin-2-yl 0 1494 4-Cl—C₆H₄ Me2-Imidazolin-2-yl 0 1495 4-Me—C₆H₄ Me 2-Imidazolin-2-yl 0 14963,5-Cl₂—C₆H₃ Me 2-Imidazolin-2-yl 0 1497 3,4-Me₂—C₆H₃ Me2-Imidazolin-2-yl 0 1498 2-Cl- Me 2-Imidazolin-2-yl 1 pyridin-2-yl 14995-CF₃- Me 2-Imidazolin-2-yl 1 pyridin-2-yl 1500 5-Cl- Me2-Imidazolin-2-yl 1 pyridin-2-yl 1501 C₆H₅ Me 2-Thiazolin-2-yl 1 15022-Cl—C₆H₄ Me 2-Thiazolin-2-yl 1 1503 3-Cl—C₆H₄ Me 2-Thiazolin-2-yl 11504 4-Cl—C₆H₄ Me 2-Thiazolin-2-yl 1 1505 2-Me—C₆H₄ Me 2-Thiazolin-2-yl1 1506 3-Me—C₆H₄ Me 2-Thiazolin-2-yl 1 1507 4-Me—C₆H₄ Me2-Thiazolin-2-yl 1 1508 2-MeO—C₆H₄ Me 2-Thiazolin-2-yl 1 1509 4-Br—C₆H₄Me 2-Thiazolin-2-yl 1 1510 3-CF₃—C₆H₄ Me 2-Thiazolin-2-yl 1 15112,4-Cl₂—C₆H₃ Me 2-Thiazolin-2-yl 1 1512 2,5-Cl₂—C₆H₃ Me 2-Thiazolin-2-yl1 1513 2,4-Me₂—C₆H₃ Me 2-Thiazolin-2-yl 1 1514 2,5-Me₂—C₆H₃ Me2-Thiazolin-2-yl 1 mp 79-82° C. 1515 C₆H₅ Me 2-Thiazolin-2-yl 0¹H-NMR(CDCl₃)δppm: 2.88(3.22)(2H, t, J=8.0), 3.90(4.29)(2H, t, J=8.0),4.06(3.95)(3H, s), 6.91- 7.58(9H, m) 1516 4-Cl—C₆H₄ Me 2-Thiazolin-2-yl0 1517 4-Me—C₆H₄ Me 2-Thiazolin-2-yl 0 1518 2-Cl-pyridin-3-yl Me2-Thiazolin-2-yl 1 1519 5-CF₃-pyridin-2-yl Me 2-Thiazolin-2-yl 1 15205-Cl-pyridin-2-yl Me 2-Thiazolin-2-yl 1 1521 C₆H₅ Me Thiazol-2-yl 1 15222-Cl—C₆H₄ Me Thiazol-2-yl 1 1523 3-Cl—C₆H₄ Me Thiazol-2-yl 1 15244-Cl—C₆H₄ Me Thiazol-2-yl 1 1525 2-Me—C₆H₄ Me Thiazol-2-yl 1 15263-Me—C₆H₄ Me Thiazol-2-yl 1 1527 4-Me—C₆H₄ Me Thiazol-2-yl 1 15282-MeO—C₆H₄ Me Thiazol-2-yl 1 1529 4-Br—C₆H₄ Me Thiazol-2-yl 1 15303-CF₃—C₆H₄ Me Thiazol-2-yl 1 1532 2,5-Cl₂—C₆H₃ Me Thiazol-2-yl 1 15332,4-Me₂—C₆H₃ Me Thiazol-2-yl 1 1534 2,5-Me₂—C₆H₃ Me Thiazol-2-yl 1 mp112-113.5° C. 1535 C₆H₅ Me Thiazol-2-yl 0 1536 4-Cl—C₆H₄ Me Thiazol-2-yl0 1537 4-Me—C₆H₄ Me Thiazol-2-yl 0 1538 2-Cl-pyridin-3-yl MeThiazol-2-yl 1 1539 5-CF₃-pyridin-2-yl Me Thiazol-2-yl 1 15405-Cl-pyridin-2-yl Me Thiazol-2-yl 1 1541 C₆H₅ Me 1-Me-pyrazol-5-yl 11542 2-Cl—C₆H₄ Me 1-Me-pyrazol-5-yl 1 1543 3-Cl—C₆H₄ Me1-Me-pyrazol-5-yl 1 1544 4-Cl—C₆H₄ Me 1-Me-pyrazol-5-yl 1 1545 2-Me—C₆H₄Me 1-Me-pyrazol-5-yl 1 1546 3-Me—C₆H₄ Me 1-Me-pyrazol-5-yl 1 15474-Me—C₆H₄ Me 1-Me-pyrazol-5-yl 1 1548 2-MeO—C₆H₄ Me 1-Me-pyrazol-5-yl 11549 4-Br—C₆H₄ Me 1-Me-pyrazol-5-yl 1 1550 2,5-Me₂—C₆H₃ Et1-Me-pyrazol-5-yl 1 Isomer A: mp 74-76° C. Isomer B: mp 84-86° C. 15512,4-Cl₂—C₆H₃ Me 1-Me-pyrazol-5-yl 1 1552 2,5-Cl₂—C₆H₃ Me1-Me-pyrazol-5-yl 1 1553 2,4-Me₂—C₆H₃ Me 1-Me-pyrazol-5-yl 1 15542,5-Me₂—C₆H₃ Me 1-Me-pyrazol-5-yl 1 Isomer A: ¹H-NMR(CDCl₃)δ ppm:2.12(3H, s), 2.24(3H, s), 3.98(3H, s), 4.12(3H, s), 4.93(2H, s),5.92(1H, d, J=1.8), 6.52(1H, s), 6.64- 7.64(7H, m) Isomer B: mp 108-110°C. 1555 C₆H₅ Me 1-Me-pyrazol-5-yl 0 1556 4-Cl—C₆H₄ Me 1-Me-pyrazol-5-yl0 1557 4-Me—C₆H₄ Me 1-Me-pyrazol-5-yl 0 1558 2-Cl-pyridin-3-yl Me1-Me-pyrazol-5-yl 1 1559 5-CF₃-pyridin-2-yl Me 1-Me-pyrazol-5-yl 1 15605-Cl-pyridin-2-yl Me 1-Me-pyrazol-5-yl 1 1561 C₆H₅ Me1-Me-1,2,4-triazol- 1 ¹H-NMR(CDCl₃)δppm: 5-yl 4.00(3H, s), 4.03(3H, s),4.92(2H, s), 6.74-6.94(3H, m), 7.18-7.57(5H, m), 7.83(1H, s) 15622-Cl—C₆H₄ Me 1-Me-1,2,4-triazol- 1 5-yl 1563 3-Cl—C₆H₄ Me1-Me-1,2,4-triazol- 1 5-yl 1564 4-Cl—C₆H₄ Me 1-Me-1,2,4-triazol- 1 mp113-114° C. 5-yl 1565 2-Me—C₆H₄ Me 1-Me-1,2,4-triazol- 1 5-yl 15663-Me—C₆H₄ Me 1-Me-1,2,4-triazol- 1 5-yl 1567 4-Me—C₆H₄ Me1-Me-1,2,4-triazol- 1 5-yl 1568 2-MeO—C₆H₄ Me 1-Me-1,2,4-triazol- 1 5-yl1569 4-Br—C₆H₄ Me 1-Me-1,2,4-triazol- 1 5-yl 1570 3-CF₃—C₆H₄ Me1-Me-1,2,4-triazol- 1 5-yl 1571 2,4-Cl₂—C₆H₃ Me 1-Me-1,2,4-triazol- 15-yl 1572 2,5-Cl₂—C₆H₃ Me 1-Me-1,2,4-triazol- 1 5-yl 1573 2,4-Me₂—C₆H₃Me 1-Me-1,2,4-triazol- 1 5-yl 1574 2,5-Me₂—C₆H₃ Me 1-Me-1,2,4-triazol- 1mp 101-102° C. 5-yl 1575 C₆H₅ Me 1-Me-1,2,4-triazol- 0 3.98(6H, s),6.85-7.48(9H, m), 5-yl 7.80(1H, s) 1576 4-Cl—C₆H₄ Me 1-Me-1,2,4-triazol-0 5-yl 1577 4-Me—C₆H₄ Me 1-Me-1,2,4-triazol- 0 5-yl 15782-Cl-pyridin-3-yl Me 1-Me-1,2,4-triazol- 1 mp 99-100° C. 5-yl 15795-CF₃-pyridin-2-yl Me 1-Me-1,2,4-triazol- 1 5-yl 1580 5-Cl-pyridin-2-ylMe 1-Me-1,2,4-triazol- 1 5-yl 1581 C₆H₅ Me 1,2,4-Oxadiazol-5-yl 1 mp109.0-110.0° C. 1582 2-Cl—C₆H₄ Me 1,2,4-Oxadiazol-5-yl 1 1583 3-Cl—C₆H₄Me 1,2,4-Oxadiazol-5-yl 1 1584 4-Cl—C₆H₄ Me 1,2,4-Oxadiazol-5-yl 1 mp96-97.5° C. 1585 2-Me—C₆H₄ Me 1,2,4-Oxadiazol-5-yl 1 1586 3-Me—C₆H₄ Me1,2,4-Oxadiazol-5-yl 1 1587 4-Me—C₆H₄ Me 1,2,4-Oxadiazol-5-yl 1 15882-MeO—C₆H₄ Me 1,2,4-Oxadiazol-5-yl 1 1589 4-Br—C₆H₄ Me1,2,4-Oxadiazol-5-yl 1 1590 2,5-Me₂—C₆H₃ Me 1,2,4-Oxadiazol-5-yl 1 mp111.5-112.5° C. 1591 2,4-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-5-yl 1 15922,5-Cl₂—C₆H₃ Me 1,2,4-Oxadiazol-5-yl 1 1593 2,4-Me₂—C₆H₃ Me1,2,4-Oxadiazol-5-yl 1 1594 2,5-Me₂—C₆H₃ Me 1,2,4-Oxadiazol-5-yl 1 mp75-76° C. 1595 C₆H₅ Me 1,2,4-Oxadiazol-5-yl 0 mp 115.5-116.5° C. 15964-Cl—C₆H₄ Me 1,2,4-Oxadiazol-5-yl 0 1597 4-Me—C₆H₄ Me1,2,4-Oxadiazol-5-yl 0 1598 2-Cl-pyridin-3-yl Me 1,2,4-Oxadiazol-5-yl 11599 5-CF₃-pyridin-2-yl Me 1,2,4-Oxadiazol-5-yl 1 1600 5-Cl-pyridin-2-ylMe 1,2,4-Oxadiazol-5-yl 1 1601 C₆H₅ Me 2-Thienyl 1 1602 2-Cl—C₆H₄ Me2-Thienyl 1 1603 3-Cl—C₆H₄ Me 2-Thienyl 1 1604 4-Cl—C₆H₄ Me 2-Thienyl 11605 2-Me—C₆H₄ Me 2-Thienyl 1 1606 3-Me—C₆H₄ Me 2-Thienyl 1 16074-Me—C₆H₄ Me 2-Thienyl 1 1608 2-MeO—C₆H₄ Me 2-Thienyl 1 1609 4-Br—C₆H₄Me 2-Thienyl 1 1610 3-CF₃—C₆H₄ Me 2-Thienyl 1 1611 2,4-Cl₂—C₆H₃ Me2-Thienyl 1 1612 2,5-Cl₂—C₆H₃ Me 2-Thienyl 1 1613 2,4-Me₂—C₆H₃ Me2-Thienyl 1 1614 2,5-Me₂—C₆H₃ Me 2-Thienyl 1 Isomer A: mp 81-84° C.Isomer B: mp 106-107° C. 1615 C₆H₅ Me 2-Thienyl 0 1616 4-Cl—C₆H₄ Me2-Thienyl 0 1617 4-Me—C₆H₄ Me 2-Thienyl 0 1618 2-Cl-pyridin-3-yl Me2-Thienyl 1 1619 5-CF₃-pyridin-2-yl Me 2-Thienyl 1 16205-Cl-pyridin-2-yl Me 2-Thienyl 1 1621 C₆H₅ Me 2-Furyl 1 1622 2-Cl—C₆H₄Me 2-Furyl 1 1623 3-Cl—C₆H₄ Me 2-Furyl 1 1624 4-Cl—C₆H₄ Me 2-Furyl 11625 2-Me—C₆H₄ Me 2-Furyl 1 1626 3-Me—C₆H₄ Me 2-Furyl 1 1627 4-Me—C₆H₄Me 2-Furyl 1 1628 2-MeO—C₆H₄ Me 2-Furyl 1 1629 4-Br—C₆H₄ Me 2-Furyl 11630 3-CF₃—C₆H₄ Me 2-Furyl 1 1631 2,4-Cl₂—C₆H₃ Me 2-Furyl 1 16322,5-Cl₂—C₆H₃ Me 2-Furyl 1 1633 2,4-Me₂—C₆H₃ Me 2-Furyl 1 16342,5-Me₂—C₆H₃ Me 2-Furyl 1 Isomer A: mp 81-82° C. Isomer B: mp 110-112°C. 1635 C₆H₅ Me 2-Furyl 0 1636 4-Cl—C₆H₄ Me 2-Furyl 0 1637 4-Me—C₆H₄ Me2-Furyl 0 1638 2-Cl-pyridin-3-yl Me 2-Furyl 1 1639 5-CF₃-pyridin-2-yl Me2-Furyl 1 1640 5-Cl-pyridin-2-yl Me 2-Furyl 1 1641 C₆H₅ Me3-Me-isothiazol-5-yl 1 1642 2-Cl—C₆H₄ Me Isothiazol-5-yl 1 16433-Cl—C₆H₄ Me Isothiazol-5-yl 1 1644 4-Cl—C₆H₄ Me 3-Me-isothiazol-5-yl 11645 2-Me—C₆H₄ Me 3-Me-isothiazol-5-yl 1 1646 3-Me—C₆H₄ MeIsothiazol-5-yl 1 1647 4-Me—C₆H₄ Me Isothiazol-5-yl 1 1648 2-MeO—C₆H₄ MeIsothiazol-5-yl 1 1649 4-Br—C₆H₄ Me Isothiazol-5-yl 1 1650 2,5-Me₂—C₆H₄Me Isothiazol-5-yl 1 1651 2,4-Cl₂—C₆H₃ Me Isothiazol-5-yl 1 16522,5-Cl₂—C₆H₃ Me Isothiazol-5-yl 1 1653 2,4-Me₂—C₆H₃ Me Isothiazol-5-yl 11654 2,5-Me₂—C₆H₃ Me 3-Me-isothiazol-5-yl 1 ¹H-NMR(CDCl₃)δppm: 2.06(3H,s), 2.23(3H, s), 2.40(3H, s), 4.21(3H, s), 5.01(2H, s), 6.51(1H, s),6.60- 6.65(1H, m), 6.71(1H, s), 6.96(1H, d, J=7.9), 7.37- 7.71(4H, m)1655 C₆H₅ Me Isothiazol-5-yl 0 1656 4-Cl—C₆H₄ Me Isothiazol-5-yl 0 16574-Me—C₆H₄ Me Isothiazol-5-yl 0 1658 2-Cl-pyridin-3-yl Me Isothiazol-5-yl1 1659 5-CF₃-pyridin-2-yl Me Isothiazol-5-yl 1 1660 5-Cl-pyridin-2-yl MeIsothiazol-5-yl 1 1661 C₆H₅ Et Isoxazol-3-yl 1 ¹H-NMR(CDCl₃)δppm:1.35(1.28)(3H, t, J=7.3), 4.31(4.26)(2H, q, J=7.3), 5.06(4.98)(2H, s),6.81- 7.60(10H, m), 8.46(8.38)(1H, d, J=1.8) 1662 2-Cl—C₆H₄ EtIsoxazol-3-yl 1 1663 3-Cl—C₆H₄ Et Isoxazol-3-yl 1 1664 4-Cl—C₆H₄ EtIsoxazol-3-yl 1 1665 2-Me—C₆H₄ Et Isoxazol-3-yl 1 ¹H-NMR(CDCl₃)δppm:1.36(1.28)(3H, t, J=7.3), 2.20(2.18)(3H, s), 4.23- 4.37(2H, m),5.04(4.98)(2, s), 6.68-7.63(9H, m), 8.44(8.38)(1H, d, J=1.8) 16663-Me—C₆H₄ Et Isoxazol-3-yl 1 1667 2-Me—C₆H₄ Allyl Isoxazol-3-yl 1¹H-NMR(CDCl₃)δppm: 2.20(2.17)(3H, s), 4.69- 4.78(2H, m), 5.05(4.98)(2H,s), 5.18-5.38(2H, m), 5.92- 6.08(1H, m), 6.69-7.63(9H, m),8.45(8.38)(1H, d, J=1.8) 1668 2-MeO—C₆H₄ Et Isoxazol-3-yl 1 16694-Br—C₆H₄ Et Isoxazol-3-yl 1 1670 3-CF₃—C₆H₄ Et Isoxazol-3-yl 1 16712,4-Cl₂—C₆H₃ Et Isoxazol-3-yl 1 1672 2,5-Cl₂—C₆H₃ Et Isoxazol-3-yl 11673 2,4-Me₂—C₆H₃ Et Isoxazol-3-yl 1 1674 2,5-Me₂—C₆H₃ Et Isoxazol-3-yl1 ¹H-NMR(CDCl₃)δppm: 1.37(1.29)(3H, t, J=7.3), 2.16(2.13)(3H, s),2.25(2.22)(3H, s), 4.23- 4.38(2H, m), 5.03(4.96)(2H, s), 6.53-7.64(8H,m), 8.45(8.39)(1H, d, J=1.8) 1675 C₆H₅ Et Isoxazol-3-yl 0 1676 4-Cl—C₆H₄Et Isoxazol-3-yl 0 1677 4-Me—C₆H₄ Et Isoxazol-3-yl 0 16782-Cl-pyridin-3-yl Et Isoxazol-3-yl 1 1679 5-CF₃-pyridin-2-yl EtIsoxazol-3-yl 1 1680 5-Cl-pyridin-2-yl Et Isoxazol-3-yl 1 1681 C₆H₅ Me1,3,4-Thiadiazol-2-yl 1 1682 2-Cl—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 1 16833-Cl—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 1 1684 4-Cl—C₆H₄ Me1,3,4-Thiadiazol-2-yl 1 1685 2-Me—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 1 16863-Me—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 1 1687 4-Me—C₆H₄ Me1,3,4-Thiadiazol-2-yl 1 1688 2-MeO—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 1 16894-Br—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 1 1690 3-CF₃—C₆H₄ Me1,3,4-Thiadiazol-2-yl 1 1691 2,4-Cl₂—C₆H₃ Me 1,3,4-Thiadiazol-2-yl 11692 2,5-Cl₂—C₆H₃ Me 1,3,4-Thiadiazol-2-yl 1 1693 2,4-Me₂—C₆H₃ Me1,3,4-Thiadiazol-2-yl 1 1694 2,5-Me₂—C₆H₃ Me 1,3,4-Thiadiazol-2-yl 11695 C₆H₅ Me 1,3,4-Thiadiazol-2-yl 0 1696 4-Cl—C₆H₄ Me1,3,4-Thiadiazol-2-yl 0 1697 4-Me—C₆H₄ Me 1,3,4-Thiadiazol-2-yl 0 16982-Cl-pyridin-3-yl Me 1,3,4-Thiadiazol-2-yl 1 1699 5-CF₃-pyridin-2-yl Me1,3,4-Thiadiazol-2-yl 1 1700 5-Cl-pyridin-2-yl Me 1,3,4-Thiadiazol-2-yl1 1701 C₆H₅ Me Oxazol-2-yl 1 1702 2-Cl—C₆H₄ Me Oxazol-2-yl 1 17033-Cl—C₆H₄ Me Oxazol-2-yl 1 1704 4-Cl—C₆H₄ Me Oxazol-2-yl 1 17052-Me—C₆H₄ Me Oxazol-2-yl 1 1706 3-Me—C₆H₄ Me Oxazol-2-yl 1 17074-Me—C₆H₄ Me Oxazol-2-yl 1 1708 2-MeO—C₆H₄ Me Oxazol-2-yl 1 17094-Br—C₆H₄ Me Oxazol-2-yl 1 1710 3-CF₃—C₆H₄ Me Oxazol-2-yl 1 17112,4-Cl₂—C₆H₃ Me Oxazol-2-yl 1 1712 2,5-Cl₂—C₆H₃ Me Oxazol-2-yl 1 17132,4-Me₂—C₆H₃ Me Oxazol-2-yl 1 1714 2,5-Me₂—C₆H₃ Me Oxazol-2-yl 1 1715C₆H₅ Me Oxazol-2-yl 0 1716 4-Cl—C₆H₄ Me Oxazol-2-yl 0 1717 4-Me—C₆H₄ MeOxazol-2-yl 0 1718 2-Cl-pyridin-3-yl Me Oxazol-2-yl 1 17195-CF₃-pyridin-2-yl Me Oxazol-2-yl 1 1720 5-Cl-pyridin-2-yl MeOxazol-2-yl 1 1721 C₆H₅ Me Oxazol-5-yl 1 H-NMR(CDCl₃)δppm: 4.00(3.85),(3H, s), 4.98(4.97)(2H, s), 6.78- 7.66(10H, m), 7.92(1H, s) 17222-Cl—C₆H₄ Me Oxazol-5-yl 1 1723 3-Cl—C₆H₄ Me Oxazol-5-yl 1 17244-Cl—C₆H₄ Me Oxazol-5-yl 1 mp 71-73° C. 1725 2-Me—C₆H₄ Me Oxazol-5-yl 11726 3-Me—C₆H₄ Me Oxazol-5-yl 1 1727 4-Me—C₆H₄ Me Oxazol-5-yl 1 17282-MeO—C₆H₄ Me Oxazol-5-yl 1 1729 4-Br—C₆H₄ Me Oxazol-5-yl 1 17303-CF₃—C₆H₄ Me Oxazol-5-yl 1 3.99(3H, s), 5.01(2H, s), 6.88(1H, s),6.94-7.62(8H, m), 7.93(1H, s) 1731 2,4-Cl₂—C₆H₃ Me Oxazol-5-yl 1 17322,5-Cl₂—C₆H₃ Me Oxazol-5-yl 1 1733 2,4-Me₂—C₆H₃ Me Oxazol-5-yl 1 17342,5-Me₂—C₆H₃ Me Oxazol-5-yl 1 mp 90-91° C. 1735 C₆H₅ Me Oxazol-5-yl 0 mp76.5-77.5° C. 1736 4-Cl—C₆H₄ Me Oxazol-5-yl 0 1737 4-Me—C₆H₄ MeOxazol-5-yl 0 1738 2-Cl-pyridin-3-yl Me Oxazol-5-yl 1 17395-CF₃-pyridin-2-yl Me Oxazol-5-yl 1 1740 5-Cl-pyridin-2-yl MeOxazol-5-yl 1 1741 C₆H₅ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 1742 2-Cl—C₆H₄Me 5,5-Me₂-2- 1 isoxazolin-3-yl 1743 3-Cl—C₆H₄ Me 5,5-Me₂-2- 1isoxazolin-3-yl 1744 4-Cl—C₆H₄ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 17452-Me—C₆H₄ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 1746 3-Me—C₆H₄ Me 5,5-Me₂-2- 1isoxazolin-3-yl 1747 4-Me—C₆H₄ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 17482-MeO—C₆H₄ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 1749 4-Br—C₆H₄ Me 5,5-Me₂-2-1 isoxazolin-3-yl 1750 2,5-Me₂—C₆H₃ Et 5,5-Me₂-2- 1 ¹H-NMR(CDCl₃)δppm:isoxazolin-3-yl 1.25(1.33)(3H, t, J=7.3), 1.36(1.55)(6H, s),2.20(2.21(3H, s), 2.27(2.26) (3H, s), 3.03-3.22(2H, m), 4.15-4.27(2H,m), 4.92- 5.08(2H, m), 6.57-7.53(7H, m) 1751 2,4-Cl₂—C₆H₃ Me 5,5-Me₂-2-1 isoxazolin-3-yl 1752 2,5-Cl₂—C₆H₃ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 17532,4-Me₂—C₆H₃ Me 5,5-Me₂-2- 1 isoxazolin-3-yl 1754 2,5-Me₂—C₆H₃ Me5,5-Me₂-2- 1 mp 86-89° C. isoxazolin-3-yl 1755 C₆H₅ Me Isothiazol-5-yl 0isoxazolin-3-yl 1756 4-Cl—C₆H₄ Me Isothiazol-5-yl 0 isoxazolin-3-yl 17574-Me—C₆H₄ Me Isothiazol-5-yl 0 isoxazolin-3-yl 1758 2-Cl-pyridin-3-yl MeIsothiazol-5-yl 1 isoxazolin-3-yl 1759 5-CF₃-pyridin-2-yl MeIsothiazol-5-yl 1 isoxazolin-3-yl 1760 5-Cl-pyridin-2-yl MeIsothiazol-5-yl 1 isoxazolin-3-yl 1761 C₆H₅ Et 3-Me-isoxazol-5-yl 1 17622-Cl—C₆H₄ Et 3-Me-isoxazol-5-yl 1 1763 3-Cl—C₆H₄ Et 3-Me-isoxazol-5-yl 11764 4-Cl—C₆H₄ Et 3-Me-isoxazol-5-yl 1 Isomer A: ¹H-NMR(CDCl₃)δppm:1.38(3H, t, J=7.3), 2.16(3H, s), 2.34(3H, s), 4.37(2H, q, J=7.3),5.02(2H, s), 6.68-7.63(9H, m) Isomer B: ¹H-NMR(CDCl₃)δppm: 1.29(3H, t,J=7.3), 2.18(3H, s), 2.26(3H, s), 4.30(2H, q, J=7.3), 4.97(2H, s),5.96(1H, s), 6.70-7.67(8H, m) 1765 2-Me—C₆H₄ Et 3-Me-isoxazol-5-yl 11766 3-Me—C₆H₄ Et 3-Me-isoxazol-5-yl 1 1767 4-Me—C₆H₄ Et3-Me-isoxazol-5-yl 1 1768 2-MeO—C₆H₄ Et 3-Me-isoxazol-5-yl 1 17694-Br—C₆H₄ Et 3-Me-isoxazol-5-yl 1 1770 3-CF₃—C₆H₄ Et 3-Me-isoxazol-5-yl1 1771 2,4-Cl₂—C₆H₃ Et 3-Me-isoxazol-5-yl 1 1772 2,5-Cl₂—C₆H₃ Et3-Me-isoxazol-5-yl 1 1773 2,4-Me₂—C₆H₃ Et 3-Me-isoxazol-5-yl 1 17742,5-Me₂—C₆H₃ Et 3-Me-isoxazol-5-yl 1 1775 C₆H₅ Et 3-Me-isoxazol-5-yl 01776 4-Cl—C₆H₄ Et 3-Me-isoxazol-5-yl 0 1777 4-Me—C₆H₄ Et3-Me-isoxazol-5-yl 0 1778 2-Cl-pyridin-3-yl Et 3-Me-isoxazol-5-yl 1 17795-CF₃-pyridin-2-yl Et 3-Me-isoxazol-5-yl 1 1780 5-Cl-pyridin-2-yl Et3-Me-isoxazol-5-yl 1 1781 C₆H₅ Et 1-Me-imidazol-2-yl 1 1782 2-Cl—C₆H₄ Et1-Me-imidazol-2-yl 1 1783 3-Cl—C₆H₄ Et 1-Me-imidazol-2-yl 1 17844-Cl—C₆H₄ Et 1-Me-imidazol-2-yl 1 1785 2-Me—C₆H₄ Et 1-Me-imidazol-2-yl 11786 3-Me—C₆H₄ Et 1-Me-imidazol-2-yl 1 1787 4-Me—C₆H₄ Et1-Me-imidazol-2-yl 1 1788 2-MeO—C₆H₄ Et 1-Me-imidazol-2-yl 1 17894-Br—C₆H₄ Et 1-Me-imidazol-2-yl 1 1790 3-CF₃—C₆H₄ Et 1-Me-imidazol-2-yl1 1791 2,4-Cl₂—C₆H₃ Et 1-Me-imidazol-2-yl 1 1792 2,5-Cl₂—C₆H₃ Et1-Me-imidazol-2-yl 1 1793 2,4-Me₂—C₆H₃ Et 1-Me-imidazol-2-yl 1 17942,5-Me₂—C₆H₃ Et 1-Me-imidazol-2-yl 1 1795 C₆H₅ Et 1-Me-imidazol-2-yl 01796 4-Cl—C₆H₄ Et 1-Me-imidazol-2-yl 0 1797 4-Me—C₆H₄ Et1-Me-imidazol-2-yl 0 1798 2-Cl-pyridin-3-yl Et 1-Me-imidazol-2-yl 1 17995-CF₃-pyridin-2-yl Et 1-Me-imidazol-2-yl 1 1800 5-Cl-pyridin-2-yl Et1-Me-imidazol-2-yl 1 1801 Pyridin-2-yl Me 1-Me-2-imidazolin- 0 2-yl 18025-Cl- Me 1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1803 3-Cl- Me1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1804 6-Cl- Me 1-Me-2-imidazolin-0 pyridin-2-yl 2-yl 1805 3,5-Cl₂- Me 1-Me-2-imidazolin- 0 pyridin-2-yl2-yl 1806 5-CF₃- Me 1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1807 3-CF₃-Me 1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1808 6-CF₃-3-Cl- Me1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1809 5-CF₃-3-Cl- Me1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1810 Benzothiazol- Me1-Me-2-imidazolin- 0 2-yl 2-yl 1811 Benzoxazol- Me 1-Me-2-imidazolin- 02-yl 2-yl 1812 Quinolin-2-yl Me 1-Me-2-imidazolin- 0 2-yl 18135-CF₃-1,3,4- Me 1-Me-2-imidazolin- 0 thiadiazol-2-yl 2-yl 1814Pyrimidin-2-yl Me 1-Me-2-imidazolin- 0 2-yl 1815 6-Cl-pyrimidin-4- Me1-Me-2-imidazolin- 0 yl 2-yl 1816 5-Et-6-Me- Me 1-Me-2-imidazolin- 0pyrimidin-2-yl 2-yl 1817 6-Cl- Me 1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl1818 3,6-Me₂- Me 1-Me-2-imidazolin- 0 pyridin-2-yl 2-yl 1819 3-Ph- Me1-Me-2-imidazolin- 0 isoxazol-5-yl 2-yl 1820 5-Me- Me 1-Me-2-imidazolin-0 isoxazol-3-yl 2-yl 1821 Pyridin-2-yl Me 2-Oxazolin-2-yl 0 1822 5-Cl-Me 2-Oxazolin-2-yl 0 pyridin-2-yl 1823 3-Cl- Me 2-Oxazolin-2-yl 0pyridin-2-yl 1824 6-Cl- Me 2-Oxazolin-2-yl 0 pyridin-2-yl 1825 3,5-Cl₂-Me 2-Oxazolin-2-yl 0 ¹H-NMR(CDCl₃)δppm: pyridin-2-yl 3.97(4.06)(3H, s),3.86- 4.29(4H, m), 6.82-7.91(6H, m) 1826 5-CF₃- Me 2-Oxazolin-2-yl 0¹H-NMR(CDCl₃)δppm: pyridin-2-yl 3.78(2H, t, J=9.8), 3.98(3H, s),4.16(2H, t, J=9.8), 6.94- 7.87(6H, m), 8.43(1H, brs) 1827 3-CF₃- Me2-Oxazolin-2-yl 0 pyridin-2-yl 1828 6-CF₃-3-Cl- Me 2-Oxazolin-2-yl 0pyridin-2-yl 1829 5-CF₃-3-Cl- Me 2-Oxazolin-2-yl 0 ¹H-NMR(CDCl₃)δppm:pyridin-2-yl 3.92(2H, t, J=9.8), 3.95(3H, s), 4.28(2H, t, J=9.8), 7.14-7.95(5H, m), 8.22(1H, brs) 1830 Benzothiazol- Me 2-Oxazolin-2-yl 0¹H-NMR(CDCl₃)δppm: 2-yl 3.84(2H, t, J=9.8), 4.03(3H, s), 4.25(2H, t,J=9.8), 7.23- 7.74(8H, m) 1831 Benzoxazol- Me 2-Oxazolin-2-yl 0 mp100-103° C. 2-yl 1832 Quinolin-2-yl Me 2-Oxazolin-2-yl 0 18335-CF₃-1,3,4- Me 2-Oxazolin-2-yl 0 thiadiazol-2-yl 1834 Pyrimidin-2-yl Me2-Oxazolin-2-yl 0 1835 6-Cl-pyrimidin-4- Me 2-Oxazolin-2-yl 0 mp103-105° C. yl 1836 5-Et-6-Me- Me 2-Oxazolin-2-yl 0 pyrimidin-2-yl 18376-Cl- Me 2-Oxazolin-2-yl 0 pyridin-2-yl 1838 3,6-Me₂- Me 2-Oxazolin-2-yl0 pyridin-2-yl 1839 3-Ph- Me 2-Oxazolin-2-yl 0 isoxazol-5-yl 1840 5-Me-Me 2-Oxazolin-2-yl 0 isoxazol-3-yl 1841 Pyridin-2-yl Me2-Isoxazolin-3-yl 0 1842 5-Cl- Me 2-Isoxazolin-3-yl 0 pyridin-2-yl 18433-Cl- Me 2-Isoxazolin-3-yl 0 pyridin-2-yl 1844 6-Cl- Me2-Isoxazolin-3-yl 0 pyridin-2-yl 1845 3,5-Cl₂- Me 2-Isoxazolin-3-yl 0pyridin-2-yl 1846 5-CF₃- Me 2-Isoxazolin-3-yl 0 pyridin-2-yl 1847 3-CF₃-Me 2-Isoxazolin-3-yl 0 pyridin-2-yl 1848 6-CF₃-3-Cl- Me2-Isoxazolin-3-yl 0 pyridin-2-yl 1849 5-CF₃-3-Cl- Me 2-Isoxazolin-3-yl 0pyridin-2-yl 1850 Benzothiazol- Me 2-Isoxazolin-3-yl 0 2-yl 1851Benzoxazol- Me 2-Isoxazolin-3-yl 0 2-yl 1852 Quinolin-2-yl Me2-Isoxazolin-3-yl 0 1853 5-CF₃-1,3,4- Me 2-Isoxazolin-3-yl 0thiadiazol-2-yl 1854 Pyrimidin-2-yl Me 2-Isoxazolin-3-yl 0 18556-Cl-pyrimidin-4- Me 2-Isoxazolin-3-yl 0 yl 1856 5-Et-6-Me- Me2-Isoxazolin-3-yl 0 pyrimidin-2-yl 1857 6-Cl- Me 2-Isoxazolin-3-yl 0pyridin-2-yl 1858 3,6-Me₂- Me 2-Isoxazolin-3-yl 0 pyridin-2-yl 18593-Ph- Me 2-Isoxazolin-3-yl 0 isoxazol-5-yl 1860 5-Me- Me2-Isoxazolin-3-yl 0 isoxazol-3-yl 1861 Pyridin-2-yl Me3-Me-isoxazol-5-yl 0 1862 5-Cl- Me 3-Me-isoxazol-5-yl 0 pyridin-2-yl1863 3-Cl- Me 3-Me-isoxazol-5-yl 0 pyridin-2-yl 1864 6-Cl- Me3-Me-isoxazol-5-yl 0 pyridin-2-yl 1865 3,5-Cl₂- Me 3-Me-isoxazol-5-yl 0pyridin-2-yl 1866 5-CF₃- Me 3-Me-isoxazol-5-yl 0 pyridin-2-yl 18673-CF₃- Me 3-Me-isoxazol-5-yl 0 pyridin-2-yl 1868 6-CF₃-3-Cl- Me3-Me-isoxazol-5-yl 0 pyridin-2-yl 1869 5-CF₃-3-Cl- Me 3-Me-isoxazol-5-yl0 pyridin-2-yl 1870 Benzothiazol- Me 3-Me-isoxazol-5-yl 0 2-yl 1871Benzoxazol- Me 3-Me-isoxazol-5-yl 0 2-yl 1872 Quinolin-2-yl Me3-Me-isoxazol-5-yl 0 1873 5-CF₃-1,3,4- Me 3-Me-isoxazol-5-yl 0thiadiazol-2-yl 1874 Pyrimidin-2-yl Me 3-Me-isoxazol-5-yl 0 18756-Cl-pyrimidin-4- Me 3-Me-isoxazol-5-yl 0 yl 1876 5-Et-6-Me- Me3-Me-isoxazol-5-yl 0 pyrimidin-2-yl 1877 6-Cl- Me 3-Me-isoxazol-5-yl 0pyridin-2-yl 1878 3,6-Me₂- Me 3-Me-isoxazol-5-yl 0 pyridin-2-yl 18793-Ph- Me 3-Me-isoxazol-5-yl 0 isoxazol-5-yl 1880 5-Me- Me3-Me-isoxazol-5-yl 0 isoxazol-3-yl 1881 Pyridin-2-yl Me1-Me-imidazol-2-yl 0 1882 5-Cl- Me 1-Me-imidazol-2-yl 0 pyridin-2-yl1883 3-Cl- Me 1-Me-imidazol-2-yl 0 pyridin-2-yl 1884 6-Cl- Me1-Me-imidazol-2-yl 0 pyridin-2-yl 1885 3,5-Cl₂- Me 1-Me-imidazol-2-yl 0pyridin-2-yl 1886 5-CF₃- Me 1-Me-imidazol-2-yl 0 pyridin-2-yl 18873-CF₃- Me 1-Me-imidazol-2-yl 0 pyridin-2-yl 1888 6-CF₃-3-Cl- Me1-Me-imidazol-2-yl 0 pyridin-2-yl 1889 5-CF₃-3-Cl- Me 1-Me-imidazol-2-yl0 pyridin-2-yl 1890 Benzothiazol- Me 1-Me-imidazol-2-yl 0 2-yl 1891Benzoxazol- Me 1-Me-imidazol-2-yl 0 2-yl 1892 Quinolin-2-yl Me1-Me-imidazol-2-yl 0 1893 5-CF₃-1,3,4- Me 1-Me-imidazol-2-yl 0thiadiazol-2-yl 1894 Pyrimidin-2-yl Me 1-Me-imidazol-2-yl 0 18956-Cl-pyrimidin-4- Me 1-Me-imidazol-2-yl 0 yl 1896 5-Et-6-Me- Me1-Me-imidazol-2-yl 0 pyrimidin-2-yl 1897 6-Cl- Me 1-Me-imidazol-2-yl 0pyridin-2-yl 1898 3,6-Me₂- Me 1-Me-imidazol-2-yl 0 pyridin-2-yl 18993-Ph- Me 1-Me-imidazol-2-yl 0 isoxazol-5-yl 1900 5-Me- Me1-Me-imidazol-2-yl 0 isoxazol-3-yl 1901 Pyridin-2-yl Me Isoxazol-3-yl 01902 5-Cl- Me Isoxazol-3-yl 0 pyridin-2-yl 1903 3-Cl- Me Isoxazol-3-yl 0pyridin-2-yl 1904 6-Cl- Me Isoxazol-3-yl 0 pyridin-2-yl 1905 3,5-Cl₂- MeIsoxazol-3-yl 0 pyridin-2-yl 1906 5-CF₃- Me Isoxazol-3-yl 0 pyridin-2-yl1907 3-CF₃- Me Isoxazol-3-yl 0 pyridin-2-yl 1908 6-CF₃-3-Cl- MeIsoxazol-3-yl 0 pyridin-2-yl 1909 5-CF₃-3-Cl- Me Isoxazol-3-yl 0pyridin-2-yl 1910 Benzothiazol- Me Isoxazol-3-yl 0 2-yl 1911 Benzoxazol-Me Isoxazol-3-yl 0 2-yl 1912 Quinolin-2-yl Me Isoxazol-3-yl 0 19135-CF₃-1,3,4- Me Isoxazol-3-yl 0 thiadiazol-2-yl 1914 Pyrimidin-2-yl MeIsoxazol-3-yl 0 1915 6-Cl-pyrimidin-4- Me Isoxazol-3-yl 0 yl 19165-Et-6-Me- Me Isoxazol-3-yl 0 pyrimidin-2-yl 1917 6-Cl- Me Isoxazol-3-yl0 pyridin-2-yl 1918 3,6-Me₂- Me Isoxazol-3-yl 0 pyridin-2-yl 1919 3-Ph-Me Isoxazol-3-yl 0 isoxazol-5-yl 1920 5-Me- Me Isoxazol-3-yl 0isoxazol-3-yl 1921 Pyridin-2-yl Me 5-Me-isoxazol-3-yl 0 1922 5-Cl- Me5-Me-isoxazol-3-yl 0 pyridin-2-yl 1923 3-Cl- Me 5-Me-isoxazol-3-yl 0pyridin-2-yl 1924 6-Cl- Me 5-Me-isoxazol-3-yl 0 pyridin-2-yl 19253,5-Cl₂- Me 5-Me-isoxazol-3-yl 0 pyridin-2-yl 1926 5-CF₃- Me5-Me-isoxazol-3-yl 0 pyridin-2-yl 1927 3-CF₃- Me 5-Me-isoxazol-3-yl 0pyridin-2-yl 1928 6-CF₃-3-Cl- Me 5-Me-isoxazol-3-yl 0 pyridin-2-yl 19295-CF₃-3-Cl- Me 5-Me-isoxazol-3-yl 0 pyridin-2-yl 1930 Benzothiazol- Me5-Me-isoxazol-3-yl 0 2-yl 1931 Benzoxazol- Me 5-Me-isoxazol-3-yl 0 2-yl1932 Quinolin-2-yl Me 5-Me-isoxazol-3-yl 0 1933 5-CF₃-1,3,4- Me5-Me-isoxazol-3-yl 0 thiadiazol-2-yl 1934 Pyrimidin-2-yl Me5-Me-isoxazol-3-yl 0 1935 6-Cl-pyrimidin-4- Me 5-Me-isoxazol-3-yl 0 yl1936 5-Et-6-Me- Me 5-Me-isoxazol-3-yl 0 pyrimidin-2-yl 1937 6-Cl- Me5-Me-isoxazol-3-yl 0 pyridin-2-yl 1938 3,6-Me₂- Me 5-Me-isoxazol-3-yl 0pyridin-2-yl 1939 3-Ph- Me 5-Me-isoxazol-3-yl 0 isoxazol-5-yl 1940 5-Me-Me 5-Me-isoxazol-3-yl 0 isoxazol-3-yl 1941 Pyridin-2-yl Me1,2,4-Oxadiazol-3-yl 0 1942 5-Cl- Me 1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl1943 3-Cl- Me 1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1944 6-Cl- Me1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1945 3,5-Cl₂- Me1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1946 5-CF₃- Me 1,2,4-Oxadiazol-3-yl0 pyridin-2-yl 1947 3-CF₃- Me 1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 19486-CF₃-3-Cl- Me 1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1949 5-CF₃-3-Cl- Me1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1950 Benzothiazol- Me1,2,4-Oxadiazol-3-yl 0 2-yl 1951 Benzoxazol- Me 1,2,4-Oxadiazol-3-yl 02-yl 1952 Quinolin-2-yl Me 1,2,4-Oxadiazol-3-yl 0 1953 5-CF₃-1,3,4- Me1,2,4-Oxadiazol-3-yl 0 thiadiazol-2-yl 1954 Pyrimidin-2-yl Me1,2,4-Oxadiazol-3-yl 0 1955 6-Cl-pyrimidin-4- Me 1,2,4-Oxadiazol-3-yl 0yl 1956 5-Et-6-Me- Me 1,2,4-Oxadiazol-3-yl 0 pyrimidin-2-yl 1957 6-Cl-Me 1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1958 3,6-Me₂- Me1,2,4-Oxadiazol-3-yl 0 pyridin-2-yl 1959 3-Ph- Me 1,2,4-Oxadiazol-3-yl 0isoxazol-5-yl 1960 5-Me- Me 1,2,4-Oxadiazol-3-yl 0 isoxazol-3-yl 1961Pyridin-2-yl Me 5-Me-1,2,4- 0 oxadiazol-3-yl 1962 5-Cl- Me 5-Me-1,2,4- 0pyridin-2-yl oxadiazol-3-yl 1963 3-Cl- Me 5-Me-1,2,4- 0 pyridin-2-yloxadiazol-3-yl 1964 6-Cl- Me 5-Me-1,2,4- 0 pyridin-2-yl oxadiazol-3-yl1965 3,5-Cl₂- Me 5-Me-1,2,4- 0 pyridin-2-yl oxadiazol-3-yl 1966 5-CF₃-Me 5-Me-1,2,4- 0 pyridin-2-yl oxadiazol-3-yl 1967 3-CF₃- Me 5-Me-1,2,4-0 pyridin-2-yl oxadiazol-3-yl 1968 6-CF₃-3-Cl- Me 5-Me-1,2,4- 0pyridin-2-yl oxadiazol-3-yl 1969 5-CF₃-3-Cl- Me 5-Me-1,2,4- 0pyridin-2-yl oxadiazol-3-yl 1970 Benzothiazol- Me 5-Me-1,2,4- 0 2-yloxadiazol-3-yl 1971 Benzoxazol- Me 5-Me-1,2,4- 0 2-yl oxadiazol-3-yl1972 Quinolin-2-yl Me 5-Me-1,2,4- 0 oxadiazol-3-yl 1973 5-CF₃-1,3,4- Me5-Me-1,2,4- 0 thiadiazol-2-yl oxadiazol-3-yl 1974 Pyrimidin-2-yl Me5-Me-1,2,4- 0 oxadiazol-3-yl 1975 6-Cl-pyrimidin-4- Me 5-Me-1,2,4- 0 yloxadiazol-3-yl 1976 5-Et-6-Me- Me 5-Me-1,2,4- 0 pyrimidin-2-yloxadiazol-3-yl 1977 6-Cl- Me 5-Me-1,2,4- 0 pyridin-2-yl oxadiazol-3-yl1978 3,6-Me₂- Me 5-Me-1,2,4- 0 pyridin-2-yl oxadiazol-3-yl 1979 3-Ph- Me5-Me-1,2,4- 0 isoxazol-5-yl oxadiazol-3-yl 1980 5-Me- Me 5-Me-1,2,4- 0isoxazol-3-yl oxadiazol-3-yl 1981 Pyridin-2-yl Me 1,3,4-Oxadiazol-2-yl 01982 5-Cl- Me 1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1983 3-Cl- Me1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1984 6-Cl- Me 1,3,4-Oxadiazol-2-yl 0pyridin-2-yl 1985 3,5-Cl₂- Me 1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 19865-CF₃- Me 1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1987 3-CF₃- Me1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1988 6-CF₃-3-Cl- Me1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1989 5-CF₃-3-Cl- Me1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1990 Benzothiazol- Me1,3,4-Oxadiazol-2-yl 0 2-yl 1991 Benzoxazol- Me 1,3,4-Oxadiazol-2-yl 02-yl 1992 Quinolin-2-yl Me 1,3,4-Oxadiazol-2-yl 0 1993 5-CF₃-1,3,4- Me1,3,4-Oxadiazol-2-yl 0 thiadiazol-2-yl 1994 Pyrimidin-2-yl Me1,3,4-Oxadiazol-2-yl 0 1995 6-Cl-pyrimidin-4- Me 1,3,4-Oxadiazol-2-yl 0yl 1996 5-Et-6-Me- Me 1,3,4-Oxadiazol-2-yl 0 pyrimidin-2-yl 1997 6-Cl-Me 1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1998 3,6-Me₂- Me1,3,4-Oxadiazol-2-yl 0 pyridin-2-yl 1999 3-Ph- Me 1,3,4-Oxadiazol-2-yl 0isoxazol-5-yl 2000 5-Me- Me 1,3,4-Oxadiazol-2-yl 0 isoxazol-3-yl 2001C₆H₅ Me 2-Me-2H- 1 mp 63.0-66.0° C. tetrazol-5-yl 2002 2-F—C₆H₄ Me2-Me-2H- 1 tetrazol-5-yl 2003 2-F—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20044-F—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2005 2-Cl—C₆H₄ Me 2-Me-2H- 1 mp122-123° C. tetrazol-5-yl 2006 3-Cl—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl2007 4-Cl—C₆H₄ Me 2-Me-2H- 1 mp 120-121.5° C. tetrazol-5-yl 20082-Br—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2009 3-Br—C₆H₄ Me 2-Me-2H- 1tetrazol-5-yl 2010 4-Br—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2011 3-I—C₆H₄Me 2-Me-2H- 1 tetrazol-5-yl 2012 2-Me—C₆H₄ Me 2-Me-2H- 1 mp 118-119° C.tetrazol-5-yl 2013 3-Me—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2014 4-Me—C₆H₄Me 2-Me-2H- 1 mp 102.0-103.0° C. tetrazol-5-yl 2015 2-Et—C₆H₄ Me2-Me-2H- 1 tetrazol-5-yl 2016 3-Et—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20174-Et—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2018 2-MeO—C₆H₄ Me 2-Me-2H- 1tetrazol-5-yl 2019 2-MeO—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20204-MeO—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2021 2-CF₃—C₆H₄ Me 2-Me-2H- 1tetrazol-5-yl 2022 3-CF₃—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20234-CF₃—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2024 2,4-F₂—C₆H₃ Me 2-Me-2H- 1tetrazol-5-yl 2025 2,5-F₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 20262,6-F₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 2027 3,4-F₂—C₆H₃ Me 2-Me-2H- 1tetrazol-5-yl 2028 3,5-F₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 20292,3-Cl₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 2030 2,4-Cl₂—C₆H₃ Me 2-Me-2H- 1tetrazol-5-yl 2031 2,5-Cl₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 20323,4-Cl₂—C₆H₃ Me 2-Me-2H- 1 mp 98-99° C. tetrazol-5-yl 2033 3,5-Cl₂—C₆H₃Me 2-Me-2H- 1 tetrazol-5-yl 2034 2,3-Me₂—C₆H₃ Me 2-Me-2H- 1tetrazol-5-yl 2035 2,4-Me₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 20362,5-Me₂—C₆H₃ Me 2-Me-2H- 1 mp 131-132° C. tetrazol-5-yl 20373,4-Me₂—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 2038 3,5-Me₂—C₆H₃ Me 2-Me-2H- 1tetrazol-5-yl 2039 2-Cl-4-Me—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 20402-Cl-5-Me—C₆H₃ Me 2-Me-2H- 1 tetrazol-5-yl 2041 4-Cl-2-Me—C₆H₃ Me2-Me-2H- 1 mp 135-136.5° C. tetrazol-5-yl 2042 4-Cl-3-Me—C₆H₃ Me2-Me-2H- 1 tetrazol-5-yl 2043 3-Ph—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20444-Ph—C₆H₄ Me 2-Me-2H- 1 mp 108.0-110.0° C. tetrazol-5-yl 20453-i-PrO—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2046 3-i-Pr—C₆H₄ Me 2-Me-2H- 1tetrazol-5-yl 2047 4-i-Pr—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20483-t-Bu—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2049 2-MeS—C₆H₄ Me 2-Me-2H- 1tetrazol-5-yl 2050 4-MeS—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 20512,3,6-F₃—C₆H₂ Me 2-Me-2H- 1 tetrazol-5-yl 2052 2,4,5-Cl₃—C₆H₂ Me2-Me-2H- 1 tetrazol-5-yl 2053 3-PhO—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl2054 3,4,5-(MeO₃— Me 2-Me-2H- 1 C₆H₂ tetrazol-5-yl 2055 2,3,5-Me₃—C₆H₂Me 2-Me-2H- 1 tetrazol-5-yl 2056 3,4,5-Me₃—C₆H₂ Me 2-Me-2H- 1tetrazol-5-yl 2057 C₆F₅ Me 2-Me-2H- 1 tetrazol-5-yl 2058 4-Cl-3-Et—C₆H₃Me 2-Me-2H- 1 tetrazol-5-yl 2059 3-EtO—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl2060 4-EtO—C₆H₄ Me 2-Me-2H- 1 tetrazol-5-yl 2061 C₆H₅ Me 2-Me-2H- 0tetrazol-5-yl 2062 4-F—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 2063 3-Cl—C₆H₄Me 2-Me-2H- 0 tetrazol-5-yl 2064 4-Cl—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl2065 3-Me—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 2066 4-Me—C₆H₄ Me 2-Me-2H- 0tetrazol-5-yl 2067 4-Et—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 2068 4-NO₂—C₆H₄Me 2-Me-2H- 0 tetrazol-5-yl 2069 3,4,-Cl₂—C₆H₃ Me 2-Me-2H- 0tetrazol-5-yl 2070 3,5-Cl₂—C₆H₃ Me 2-Me-2H- 0 tetrazol-5-yl 20713,4-Me₂—C₆H₃ Me 2-Me-2H- 0 tetrazol-5-yl 2072 3,5-Me₂—C₆H₃ Me 2-Me-2H- 0tetrazol-5-yl 2073 3-PhO—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 20744-Cl-3-Et—C₆H₃ Me 2-Me-2H- 0 tetrazol-5-yl 2075 3-EtO—C₆H₄ Me 2-Me-2H- 0tetrazol-5-yl 2076 3-CF₃—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 20774-CF₃—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 2078 3-i-PrO—C₆H₄ Me 2-Me-2H- 0tetrazol-5-yl 2079 3-i-Pr—C₆H₄ Me 2-Me-2H- 0 tetrazol-5-yl 20804-Cl-3-Me—C₆H₃ Me 2-Me-2H- 0 tetrazol-5-yl 2081 Pyridin-2-yl Me 2-Me-2H-1 tetrazol-5-yl 2082 Pyridin-3-yl Me 2-Me-2H- 1 tetrazol-5-yl 2083 5-Cl-Me 2-Me-2H- 1 pyridin-2-yl tetrazol-5-yl 2084 3-Cl- Me 2-Me-2H- 1pyridin-2-yl tetrazol-5-yl 2085 6-Cl- Me 2-Me-2H- 1 pyridin-2-yltetrazol-5-yl 2086 2-Cl- Me 2-Me-2H- 1 pyridin-2-yl tetrazol-5-yl 20875-CF₃- Me 2-Me-2H- 1 pyridin-2-yl tetrazol-5-yl 2088 3-CF₃- Me 2-Me-2H-1 pyridin-2-yl tetrazol-5-yl 2089 6-CF₃-3-Cl Me 2-Me-2H- 1 pyridin-2-yltetrazol-5-yl 2090 5-CF₃-3-Cl Me 2-Me-2H- 1 pyridin-2-yl tetrazol-5-yl2091 Benzothiazol- Me 2-Me-2H- 1 2-yl tetrazol-5-yl 2092 Benzoxazol- Me2-Me-2H- 1 2-yl tetrazol-5-yl 2093 Quinolin-2-yl Me 2-Me-2H- 1tetrazol-5-yl 2094 5-CF₃-1,3,4- Me 2-Me-2H- 1 thiadiazol-2-yltetrazol-5-yl 2095 Pyimidin-2-yl Me 2-Me-2H- 1 tetrazol-5-yl 20965-Cl-6-Me- Me 2-Me-2H- 1 pyrimidin-4-yl tetrazol-5-yl 2097 5-Et-6-Me- Me2-Me-2H- 1 pyrimidin-4-yl tetrazol-5-yl 2098 6-Cl- Me 2-Me-2H- 1pyrazin-2-yl tetrazol-5-yl 2099 3,6-Me₂- Me 2-Me-2H- 1 pyrazin-2-yltetrazol-5-yl 2100 5-Me- Me 2-Me-2H- 1 isoxazol-3-yl tetrazol-5-yl No R¹R³ R⁴ n Physical data 2101 C₆H₅ 1,2,4-Oxadiazol-3-yl 5-Cl 1 21022-Cl—C₆H₄ 1,2,4-Oxadiazol-3-yl 5-Cl 1 2103 2-Me—C₆H₄1,2,4-Oxadiazol-3-yl 5-Cl 1 2104 2,5-Me₂—C₆H₃ 1,2,4-Oxadiazol-3-yl 5-Cl1 2105 4-Cl-2-Me—C₆H₄ 1,2,4-Oxadiazol-3-yl 5-Cl 1 2106 4-Cl—C₆H₄1,2,4-Oxadiazol-3-yl 5-Cl 0 2107 4-Me—C₆H₄ 1,2,4-Oxadiazol-3-yl 5-Cl 02108 C₆H₅ 1,2,4-Oxadiazol-3-yl 5-Cl 0 2109 5-CF₃- 1,2,4-Oxadiazol-3-yl5-Cl 1 pyridin-2-yl 2110 5-CF₃- 1,2,4-Oxadiazol-3-yl 5-Cl 0 pyridin-2-yl2111 C₆H₅ 5-Me-1,2,4- 5-Cl 1 oxadiazol-3-yl 2112 2-Cl—C₆H₄ 5-Me-1,2,4-5-Cl 1 oxadiazol-3-yl 2113 2-Me—C₆H₄ 5-Me-1,2,4- 5-Cl 1 oxadiazol-3-yl2114 2,5-Me₂—C₆H₃ 5-Me-1,2,4- 5-Cl 1 oxadiazol-3-yl 2115 4-Cl-2-Me—C₆H₄5-Me-1,2,4- 5-Cl 1 oxadiazol-3-yl 2116 4-Cl—C₆H₄ 5-Me-1,2,4- 5-Cl 0oxadiazol-3-yl 2117 4-Me—C₆H₄ 5-Me-1,2,4- 5-Cl 0 oxadiazol-3-yl 2118C₆H₅ 5-Me-1,2,4- 5-Cl 0 oxadiazol-3-yl 2119 5-CF₃- 5-Me-1,2,4- 5-Cl 1pyridin-2-yl oxadiazol-3-yl 2120 5-CF₃- 5-Me-1,2,4- 5-Cl 0¹H-NMR(CDCl₃)δppm: pyridin-2-yl oxadiazol-3-yl 2.46(3H, s), 4.03(3H, s),6.77(1H, d, J=9.2), 7.16(1H, d, J=9.2), 7.44-7.86(3H, m), 8.36(1H, d,J=1.8) 2121 C₆H₅ Isoxazol-3-yl 5-Cl 1 2122 2-Cl—C₆H₄ Isoxazol-3-yl 5-Cl1 2123 2-Me—C₆H₄ Isoxazol-3-yl 5-Cl 1 2124 2,5-Me₂—C₆H₃ Isoxazol-3-yl5-Cl 1 2125 4-Cl-2-Me—C₆H₃ Isoxazol-3-yl 5-Cl 1 2126 4-Cl—C₆H₄Isoxazol-3-yl 5-Cl 0 2127 4-Me—C₆H₄ Isoxazol-3-yl 5-Cl 0 2128 C₆H₅Isoxazol-3-yl 5-Cl 0 2129 5-CF₃- Isoxazol-3-yl 5-Cl 1 pyridin-2-yl 21305-CF₃- Isoxazol-3-yl 5-Cl 0 pyridin-2-yl 2131 C₆H₅ 3-Me-isoxazol-5-yl5-Cl 1 2132 2-Cl—C₆H₄ 3-Me-isoxazol-5-yl 5-Cl 1 2133 2-Me—C₆H₄3-Me-isoxazol-5-yl 5-Cl 1 2134 2,5-Me₂—C₆H₃ 3-Me-isoxazol-5-yl 5-Cl 12135 4-Cl-2-Me—C₆H₃ 3-Me-isoxazol-5-yl 5-Cl 1 2136 4-Cl—C₆H₄3-Me-isoxazol-5-yl 5-Cl 0 2137 4-Me—C₆H₄ 3-Me-isoxazol-5-yl 5-Cl 0 2138C₆H₅ 3-Me-isoxazol-5-yl 5-Cl 0 2139 5-CF₃- 3-Me-isoxazol-5-yl 5-Cl 1pyridin-2-yl 2140 5-CF₃- 3-Me-isoxazol-5-yl 5-Cl 0 pyridin-2-yl 2141C₆H₅ 1-Me-imidazol-2-yl 5-Cl 1 2142 2-Cl—C₆H₄ 1-Me-imidazol-2-yl 5-Cl 12143 2-Me—C₆H₄ 1-Me-imidazol-2-yl 5-Cl 1 2144 2,5-Me₂—C₆H₃1-Me-imidazol-2-yl 5-Cl 1 2145 4-Cl-2-Me—C₆H₃ 1-Me-imidazol-2-yl 5-Cl 12146 4-Cl—C₆H₄ 1-Me-imidazol-2-yl 5-Cl 0 2147 4-Me—C₆H₄1-Me-imidazol-2-yl 5-Cl 0 2148 C₆H₅ 1-Me-imidazol-2-yl 5-Cl 0 21495-CF₃- 1-Me-imidazol-2-yl 5-Cl 1 pyridin-2-yl 2150 5-CF₃-1-Me-imidazol-2-yl 5-Cl 0 pyridin-2-yl 2151 C₆H₅ 1-Me-imidazol-2-yl 5-Cl1 2152 2-Cl—C₆H₄ 1-Me-imidazol-2-yl 5-Cl 1 2153 2-Me—C₆H₄1-Me-imidazol-2-yl 5-Cl 1 2154 2,5-Me₂—C₆H₃ 1-Me-imidazol-2-yl 5-Cl 12155 4-Cl-2-Me—C₆H₃ 1-Me-imidazol-2-yl 5-Cl 1 2156 4-Cl—C₆H₄1-Me-imidazol-2-yl 5-Cl 0 2157 4-Me—C₆H₄ 1-Me-imidazol-2-yl 5-Cl 0 2158C₆H₅ 1-Me-imidazol-2-yl 5-Cl 0 2159 5-CF₃- 1-Me-imidazol-2-yl 5-Cl 1pyridin-2-yl 2160 5-CF₃- 1-Me-imidazol-2-yl 5-Cl 0 pyridin-2-yl 2161C₆H₅ 1,2,4-Oxadiazol-3-yl 5-F 1 2162 2-Cl—C₆H₄ 1,2,4-Oxadiazol-3-yl 5-F1 2163 2-Me—C₆H₄ 1,2,4-Oxadiazol-3-yl 5-F 1 2164 2,5-Me₂—C₆H₃1,2,4-Oxadiazol-3-yl 5-F 1 2165 4-Cl-2-Me—C₆H₃ 1,2,4-Oxadiazol-3-yl 5-F1 2166 4-Cl—C₆H₄ 1,2,4-Oxadiazol-3-yl 5-F 0 2167 4-Me—C₆H₄1,2,4-Oxadiazol-3-yl 5-F 0 2168 C₆H₅ 1,2,4-Oxadiazol-3-yl 5-F 0 21695-CF₃- 1,2,4-Oxadiazol-3-yl 5-F 1 pyridin-2-yl 2170 5-CF₃-1,2,4-Oxadiazol-3-yl 5-F 0 pyridin-2-yl 2171 C₆H₅ 5-Me-1,2,4- 5-F 1oxadiazol-3-yl 2172 2-Cl—C₆H₄ 5-Me-1,2,4- 5-F 1 oxadiazol-3-yl 21732-Me—C₆H₄ 5-Me-1,2,4- 5-F 1 oxadiazol-3-yl 2174 2,5-Me₂—C₆H₃ 5-Me-1,2,4-5-F 1 oxadiazol-3-yl 2175 4-Cl-2-Me—C₆H₃ 5-Me-1,2,4- 5-F 1oxadiazol-3-yl 2176 4-Cl—C₆H₄ 5-Me-1,2,4- 5-F 0 oxadiazol-3-yl 21774-Me—C₆H₄ 5-Me-1,2,4- 5-F 0 oxadiazol-3-yl 2178 C₆H₅ 5-Me-1,2,4- 5-F 0oxadiazol-3-yl 2179 5-CF₃- 5-Me-1,2,4- 5-F 1 pyridin-2-yl oxadiazol-3-yl2180 5-CF₃- 5-Me-1,2,4- 5-F 0 pyridin-2-yl oxadiazol-3-yl 2181 C₆H₅Isoxazol-3-yl 5-F 1 2182 2-Cl—C₆H₄ Isoxazol-3-yl 5-F 1 2183 2-Me—C₆H₄Isoxazol-3-yl 5-F 1 2184 2,5-Me₂—C₆H₃ Isoxazol-3-yl 5-F 1 21854-Cl-2-Me—C₆H₃ Isoxazol-3-yl 5-F 1 2186 4-Cl—C₆H₄ Isoxazol-3-yl 5-F 02187 4-Me—C₆H₄ Isoxazol-3-yl 5-F 0 2188 C₆H₅ Isoxazol-3-yl 5-F 0 21895-CF₃- Isoxazol-3-yl 5-F 1 pyridin-2-yl 2190 5-CF₃- Isoxazol-3-yl 5-F 0pyridin-2-yl 2191 C₆H₅ 3-Me-isoxazol-5-yl 5-F 1 2192 2-Cl—C₆H₄3-Me-isoxazol-5-yl 5-F 1 2193 2-Me—C₆H₄ 3-Me-isoxazol-5-yl 5-F 1 21942,5-Me₂—C₆H₃ 3-Me-isoxazol-5-yl 5-F 1 2195 4-Cl-2-Me—C₆H₃3-Me-isoxazol-5-yl 5-F 1 2196 4-Cl—C₆H₄ 3-Me-isoxazol-5-yl 5-F 0 21974-Me—C₆H₄ 3-Me-isoxazol-5-yl 5-F 0 2198 C₆H₅ 3-Me-isoxazol-5-yl 5-F 02199 5-CF₃- 3-Me-isoxazol-5-yl 5-F 1 pyridin-2-yl 2200 5-CF₃-3-Me-isoxazol-5-yl 5-F 0 pyridin-2-yl 2201 C₆H₅ 5-Me-1,3,4- H 1oxadiazol-2-yl 2202 2-Cl—C₆H₄ 5-Me-1,3,4- H 1 oxadiazol-2-yl 22034-Cl—C₆H₄ 5-Me-1,3,4- H 1 oxadiazol-2-yl 2204 2-Me—C₆H₄ 5-Me-1,3,4- H 1oxadiazol-2-yl 2205 4-Me—C₆H₄ 5-Me-1,3,4- H 1 oxadiazol-2-yl 22063-CF₃—C₆H₄ 5-Me-1,3,4- H 1 oxadiazol-2-yl 2207 2,5-Me₂—C₆H₃ 5-Me-1,3,4-H 1 mp 134.0-139.0° C. oxadiazol-2-yl 2208 4-Cl-2-Me—C₆H₃ 5-Me-1,3,4- H1 ¹H-NMR(CDCl₃)δppm: oxadiazol-2-yl 2.12(3H, s), 2.58(3H, s), 4.05(3H,s), 4.97(2H, s), 6.63(1H, d, J=8.5), 6.99-7.64(6H, m) 2209 2,5-Cl₂—C₆H₃5-Me-1,3,4- H 1 oxadiazol-2-yl 2210 5-CF₃ 5-Me-1,3,4- H 1 pyridin-2-yloxadiazol-2-yl 2211 C₆H₅ Thiazolidin-2-yl H 1 2212 2-Cl—C₆H₄Thiazolidin-2-yl H 1 2213 4-Cl—C₆H₄ Thiazolidin-2-yl H 1 2214 2-Me—C₆H₄Thiazolidin-2-yl H 1 2215 4-Me—C₆H₄ Thiazolidin-2-yl H 1 2216 3-CF₃—C₆H₄Thiazolidin-2-yl H 1 2217 2,5-Me₂—C₆H₃ Thiazolidin-2-yl H 1¹H-NMR(CDCl₃)δppm: 2.28(6H, s), 2.40(1H, brs), 2.81-3.06(3H, m),3.38-3.55(1H, m), 3.87(3H, s), 4.85-5.50(3H, m), 6.67-7.64(7H, m) 22184-Cl-2-Me—C₆H₃ Thiazolidin-2-yl H 1 2219 2,5-Cl₂—C₆H₃ Thiazolidin-2-yl H1 mp 121.0-122.0° C. 2220 5-CF₃- Thiazolidin-2-yl H 1 pyridin-2-yl 2221C₆H₅ 3,5-Me₂- H 1 ¹H-NMR(CDCl₃)δppm: isoxazol-4-yl 2.00(1.96)(3H, s),2.17(3H, s), 3.94(3.91)(3H, s), 5.19(4.94)(2H, s), 6.83-7.66(9H, m) 22222-Cl—C₆H₄ 3,5-Me₂- H 1 isoxazol-4-yl 2223 4-Cl—C₆H₄ 3,5-Me₂- H 1isoxazol-4-yl 2224 2-Me—C₆H₄ 3,5-Me₂- H 1 isoxazol-4-yl 2225 4-Me—C₆H₄3,5-Me₂- H 1 isoxazol-4-yl 2226 3-CF₃—C₆H₄ 3,5-Me₂- H 1 isoxazol-4-yl2227 2,5-Me₂—C₆H₃ 3,5-Me₂- H 1 ¹H-NMR(CDCl₃)δppm: 1.95- isoxazol-4-yl2.28(12H, m), 3.94(3.99)(3H, s), 4.93(5.18)(2H, s), 6.57-7.71(7H, m)2228 4-Cl-2-Me—C₆H₃ 3,5-Me₂- H 1 ¹H-NMR(CDCl₃)δppm: isoxazol-4-yl1.95(1.98)(3H, s), 2.13-2.23(6H, m), 3.93(3.98)(3H, s), 4.91(5.17)(2H,s), 6.65-6.72(2H, m), 7.01-7.66(5H, m), 2229 2,5-Cl₂—C₆H₃ 3,5-Me₂- H 1isoxazol-4-yl 2230 5-CF₃-3,5-Me₂- H 1 pyridin-2-yl isoxazol-4-yl 2231C₆H₅ 1,3-Dioxolan-2-yl H 1 2232 2-Cl—C₆H₄ 1,3-Dioxolan-2-yl H 1 22334-Cl—C₆H₄ 1,3-Dioxolan-2-yl H 1 2234 2-Me—C₆H₄ 1,3-Dioxolan-2-yl H 12235 4-Me—C₆H₄ 1,3-Dioxolan-2-yl H 1 2236 3-CF₃—C₆H₄ 1,3-Dioxolan-2-yl H1 2237 2,5-Me₂—C₆H₃ 1,3-Dioxolan-2-yl H 1 ¹H-NMR(CDCl₃)δppm: 2.28(3H,s), 2.29(3H, s), 3.59-3.85 (4H, m), 3.92(3H, s), 5.04(1H, s), 5.09 (1H,s), 5.63(1H, s), 6.66- 7.62(7H, m) 2238 4-Cl-2-Me—C₆H₃ 1,3-Dioxolan-2-ylH 1 2239 2,5-Cl₂—C₆H₃ 1,3-Dioxolan-2-yl H 1 2240 5-CF₃-1,3-Dioxolan-2-yl H 1 2241 C₆H₅ 3-Me-2-isoxazolin- H 1 5-yl 22422-Cl—C₆H₄ 3-Me-2-isoxazolin- H 1 5-yl 2243 4-Cl—C₆H₄ 3-Me-2-isoxazolin-H 1 5-yl 2244 2-Me—C₆H₄ 3-Me-2-isoxazolin- H 1 ¹H-NMR(CDCl₃)δppm: 5-yl1.88(3H, s), 2.26(2.27)(3H, s), 2.84-3.38(2H, m), 3.95(3.87)(3H, s),4.87-5.38(2H, m), 5.74- 5.81(1H, m), 6.84-6.89(2H, m), 7.11-7.60(6H, m)2245 4-Me—C₆H₄ 3-Me-2-isoxazolin- H 1 5-yl 2246 3-CF₃—C₆H₄3-Me-2-isoxazolin- H 1 5-yl 2247 2,5-Me₂—C₆H₃ 3-Me-2-isoxazolin- H 1¹H-NMR(CDCl₃)δppm: 5-yl 1.88(3H, s), 2.20(2.22)(3H, s), 2.30(3H, s),2.84-3.37(2H, m), 3.96(3.88)(3H, s), 4.85-5.35(2H, m), 5.74-5.82(1H, m),6.67- 6.69(2H, m), 7.01(5H, m) 2248 4-Cl-2-Me—C₆H₃ 3-Me-2-isoxazolin- H1 5-yl 2249 2,5-Cl₂—C₆H₃ 3-Me-2-isoxazolin- H 1 5-yl 2250 5-CF₃-3-Me-2-isoxazolin- H 1 pyridin-2-yl 5-yl 2251 C₆H₅ 4-Me-1,2,3- H 1 mp90.5-91.5° C. thiadiazol-5-yl 2252 2-Cl—C₆H₄ 4-Me-1,2,3- H 1thiadiazol-5-yl 2253 4-Cl—C₆H₄ 4-Me-1,2,3- H 1 thiadiazol-5-yl 22542-Me—C₆H₄ 4-Me-1,2,3- H 1 thiadiazol-5-yl 2255 4-Me—C₆H₄ 4-Me-1,2,3- H 1thiadiazol-5-yl 2256 3-CF₃—C₆H₄ 4-Me-1,2,3- H 1 thiadiazol-5-yl 22572,5-Me₂—C₆H₃ 4-Me-1,2,3- H 1 ¹H-NMR(CDCl₃)δppm: thiadiazol-5-yl 2.01(3H,s), 2.14(3H, s), 2.25(3H, s), 4.18(3H, s), 4.98(2H, s), 6.51(1H, s),6.65(1H, d, J=7.9), 6.96(1H, d, J=7.3), 7.24-7.96(4H, m) 22584-Cl-2-Me—C₆H₃ 4-Me-1,2,3- H 1 thiadiazol-5-yl 2259 2,5-Cl₂—C₆H₃4-Me-1,2,3- H 1 thiadiazol-5-yl 2260 5-CF₃-4-Me-1,2,3- H 1 pyridin-2-ylthiadiazol-5-yl 2261 3,5-Cl₂- Isoxazol-3-yl H 0 pyridin-2-yl 22623,5-Cl₂- Isoxazol-5-yl H 0 pyridin-2-yl 2263 3,5-Cl₂- 5-Me- H 0pyridin-2-yl isoxazol-3-yl 2264 3,5-Cl₂- 3-Me- H 0 pyridin-2-ylisoxazol-5-yl 2265 3,5-Cl₂₋ 2-Isoxazolin-3-yl H 0 pyridin-2-yl 22663,5-Cl₂- 5-Me-2-isoxazolin- H 0 pyridin-2-yl 3-yl 2267 3,5-Cl₂-3-Me-2-isoxazolin- H 0 pyridin-2-yl 5-yl 2268 3,5-Cl₂- 2-Furyl H 0pyridin-2-yl 2269 3,5-Cl₂- Thiazolidin-2-yl H 0 pyridin-2-yl 22703,5-Cl₂- 1-Me- H 0 pyridin-2-yl imidazol-2-yl 2271 3,5-Cl₂-1,2,4-Oxadiazol- H 0 pyridin-2-yl 3-yl 2272 3,5-Cl₂- 5-Me-1,2,4- H 0pyridin-2-yl oxadiazol-3-yl 2273 3,5-Cl₂- 1,2,4-oxadiazol-5-yl H 0pyridin-2-yl 2274 3,5-Cl₂- 1,3,4-oxadiazol-2-yl H 0 pyridin-2-yl 22753,5-Cl₂- 5-Me-1,3,4- H 0 pyridin-2-yl oxadiazol-2-yl 2276 3,5-Cl₂-Isoxazol-3-yl H 1 mp 136-137° C. pyridin-2-yl 2277 3,5-Cl₂-Isoxazol-5-yl H 1 pyridin-2-yl 2278 3,5-Cl₂- 5-Me- H 1¹H-NMR(CDCl₃)δppm: pyridin-2-yl isoxazol-3-yl 2.34(3H, s), 3.97(3H, s),5.32 (2H, s), 6.36(1H, s), 7.24- 7.85(6H, m). 2279 3,5-Cl₂- 3-Me- H 1Isomer A: ¹H-NMR(CDCl₃)δppm: pyridin-2-yl isoxazol-5-yl 2.35(3H, s),4.12(3H, s), 5.40(2H, s), 6.95(1H, s), 7.37-7.86(6H, m) Isomer B:¹H-NMR(CDCl₃)δppm: 2.28(3H, s), 4.03(3H, s), 5.30(2H, s), 6.01(1H, s),7.21-7.86(6H, s) 2280 3,5-Cl₂- 2-Isoxazolin-3-yl H 1 pyridin-2-yl 22813,5-Cl₂- 5-Me-2-isoxazolin- H 1 pyridin-2-yl 3-yl 2282 3,5-Cl₂-3-Me-2-isoxazolin- H 1 pyridin-2-yl 5-yl 2283 3,5-Cl₂- 2-Furyl H 1pyridin-2-yl 2284 3,5-Cl₂- Thiazolidin-2-yl H 1 pyridin-2-yl 22853,5-Cl₂- 1-Me- H 1 pyridin-2-yl imidazol-2-yl 2286 3,5-Cl₂-1,2,4-Oxadiazol- H 1 pyridin-2-yl 3-yl 2287 3,5-Cl₂- 5-Me-1,2,4- H 1pyridin-2-yl oxadiazol-3-yl 2288 3,5-Cl₂- 1,2,4-oxadiazol-5-yl H 1pyridin-2-yl 2289 3,5-Cl₂- 1,3,4-oxadiazol-2-yl H 1 pyridin-2-yl 22903,5-Cl₂- 5-Me-1,3,4- H 1 pyridin-2-yl oxadiazol-2-yl 2291 5-Cl-3-CF₃-Isoxazol-3-yl H 0 pyridin-2-yl 2292 5-Cl-3-CF₃- Isoxazol-5-yl H 0pyridin-2-yl 2293 5-Cl-3-CF₃- 5-Me- H 0 pyridin-2-yl isoxazol-3-yl 22945-Cl-3-CF₃- 3-Me- H 0 pyridin-2-yl isoxazol-5-yl 2295 5-Cl-3-CF₃-2-Isoxazolin-3-yl H 0 pyridin-2-yl 2296 5-Cl-3-CF₃- 5-Me-2-isoxazolin- H0 pyridin-2-yl 3-yl 2297 5-Cl-3-CF₃- 3-Me-2-isoxazolin- H 0 pyridin-2-yl5-yl 2298 5-Cl-3-CF₃- 2-Furyl H 0 pyridin-2-yl 2299 5-Cl-3-CF₃-Thiazolidin-2-yl H 0 pyridin-2-yl 2300 5-Cl-3-CF₃- 1-Me- H 0pyridin-2-yl imidazol-2-yl 2301 5-Cl-3-CF₃- 1,2,4-Oxadiazol- H 0pyridin-2-yl 3-yl 2302 5-Cl-3-CF₃- 5-Me-1,2,4- H 0 pyridin-2-yloxadiazol-3-yl 2303 5-Cl-3-CF₃- 1,2,4-oxadiazol-5-yl H 0 pyridin-2-yl2304 5-Cl-3-CF₃- 1,3,4-oxadiazol-2-yl H 0 pyridin-2-yl 2305 5-Cl-3-CF₃-5-Me-1,3,4- H 0 pyridin-2-yl oxadiazol-2-yl 2306 5-Cl-3-CF₃-Isoxazol-3-yl H 1 mp 97.5-98.5° C. pyridin-2-yl 2307 5-Cl-3-CF₃-Isoxazol-5-yl H 1 pyridin-2-yl 2308 5-Cl-3-CF₃- 5-Me- H 1 mp 120-121° C.pyridin-2-yl isoxazol-3-yl 2309 5-Cl-3-CF₃- 3-Me- H 1 Isomer A:¹H-NMR(CDCl₃)δppm: pyridin-2-yl isoxazol-5-yl 2.37(3H, s), 4.14(3H, s),5.45(2H, s), 6.97(1H, s), 7.36-7.63(4H, m), 7.79(1H, d, J=2.24),8.09(1H, d, J=2.4) Isomer B: ¹H-NMR(CDCl₃)δppm: 2.28(3H, s), 4.04(3H,s), 5.33(2H, s), 6.01(1H, s), 7.20-7.56(4H, s) 7.80(1H, d, J=2.4),8.08(1H, d, J=2.4) 2310 5-Cl-3-CF₃- 2-Isoxazolin-3-yl H 1 pyridin-2-yl2311 5-Cl-3-CF₃- 5-Me-2-isoxazolin- H 1 pyridin-2-yl 3-yl 23125-Cl-3-CF₃- 3-Me-2-isoxazolin- H 1 pyridin-2-yl 5-yl 2313 5-Cl-3-CF₃-2-Furyl H 1 pyridin-2-yl 2314 5-Cl-3-CF₃- Thiazolidin-2-yl H 1pyridin-2-yl 2315 5-Cl-3-CF₃- 1-Me- H 1 pyridin-2-yl imidazol-2-yl 23165-Cl-3-CF₃- 1,2,4-Oxadiazol- H 1 pyridin-2-yl 3-yl 2317 5-Cl-3-CF₃-5-Me-1,2,4- H 1 pyridin-2-yl oxadiazol-3-yl 2318 5-Cl-3-CF₃-1,2,4-oxadiazol-5-yl H 1 pyridin-2-yl 2319 5-Cl-3-CF₃-1,3,4-oxadiazol-2-yl H 1 pyridin-2-yl 2320 5-Cl-3-CF₃- 5-Me-1,3,4- H 1pyridin-2-yl oxadiazol-2-yl No R³ R⁹ R¹⁰ Physical data 23211-Me-imidazol-2-yl 2,4-F₂—C₆H₃ Me 2322 1-Me-imidazol-2-yl 2,5-F₂—C₆H₃ Me2323 1-Me-imidazol-2-yl 3,4-F₂—C₆H₃ Me 2324 1-Me-imidazol-2-yl3,5-F₂—C₆H₃ Me 2325 1-Me-imidazol-2-yl 2,3-Cl₂—C₆H₃ Me 23261-Me-imidazol-2-yl 2,4-Cl₂—C₆H₃ Me 2327 1-Me-imidazol-2-yl 2,5-Cl₂—C₆H₃Me 2328 1-Me-imidazol-2-yl 3,4-Cl₂—C₆H₃ Me 2329 1-Me-imidazol-2-yl3,5-Cl₂—C₆H₃ Me 2330 1-Me-imidazol-2-yl 3,4-Me₂—C₆H₃ Me 23311-Me-imidazol-2-yl 2,4-Me₂—C₆H₃ Me 2332 1-Me-imidazol-2-yl 3-Ph—C₆H₄ Me2333 1-Me-imidazol-2-yl 4-Ph—C₆H₄ Me 2334 1-Me-imidazol-2-yl MorpholinoMe 2335 1-Me-imidazol-2-yl 2,6-Me₂ Me morpholino 2336 1-Me-imidazol-2-ylC₆H₅ Et 2337 1-Me-imidazol-2-yl 4-F—C₆H₄ Et 2338 1-Me-imidazol-2-yl4-Cl—C₆H₄ Et 2339 1-Me-imidazol-2-yl 4-Me—C₆H₄ Et 23401-Me-imidazol-2-yl 3,4-Cl₂—C₆H₃ Et 2341 1H-1,2,4- C₆H₅ Me Triazol-2-yl2342 1H-1,2,4- 2-F—C₆H₄ Me Triazol-2-yl 2343 1H-1,2,4- 3-F—C₆H₄ MeTriazol-2-yl 2344 1H-1,2,4- 4-F—C₆H₄ Me Triazol-2-yl 2345 1H-1,2,4-2-Cl—C₆H₄ Me Triazol-2-yl 2346 1H-1,2,4- 3-Cl—C₆H₄ Me Triazol-2-yl 23471H-1,2,4- 4-Cl—C₆H₄ Me Triazol-2-yl 2348 1H-1,2,4- 2-Br—C₆H₄ MeTriazol-2-yl 2349 1H-1,2,4- 3-Br—C₆H₄ Me Triazol-2-yl 2350 1H-1,2,4-4-Br—C₆H₄ Me Triazol-2-yl 2351 1H-1,2,4- 3-I—C₆H₄ Me Triazol-2-yl 23521H-1,2,4- 2-Me—C₆H₄ Me Triazol-2-yl 2353 1H-1,2,4- 3-Me—C₆H₄ MeTriazol-2-yl 2354 1H-1,2,4- 4-Me—C₆H₄ Me Triazol-2-yl 2355 1H-1,2,4-3-Et—C₆H₄ Me Triazol-2-yl 2356 1H-1,2,4- 4-Et—C₆H₄ Me Triazol-2-yl 23571H-1,2,4- 3-MeO—C₆H₄ Me Triazol-2-yl 2358 1H-1,2,4- 4-MeO—C₆H₄ MeTriazol-2-yl 2359 1H-1,2,4- 3-CF₃—C₆H₄ Me Triazol-2-yl 2360 1H-1,2,4-4-CF₃—C₆H₄ Me Triazol-2-yl 2361 1H-1,2,4- 2,4-F₂—C₆H₃ Me Triazol-2-yl2362 1H-1,2,4- 2,5-F₂—C₆H₃ Me Triazol-2-yl 2363 1H-1,2,4- 3,4-F₂—C₆H₃ MeTriazol-2-yl 2364 1H-1,2,4- 3,5-F₂—C₆H₃ Me Triazol-2-yl 2365 1H-1,2,4-2,3-Cl₂—C₆H₃ Me Triazol-2-yl 2366 1H-1,2,4- 2,4-Cl₂—C₆H₃ Me Triazol-2-yl2367 1H-1,2,4- 2,5-Cl₂—C₆H₃ Me Triazol-2-yl 2368 1H-1,2,4- 3,4-Cl₂—C₆H₃Me Triazol-2-yl 2369 1H-1,2,4- 3,5-Cl₂—C₆H₃ Me Triazol-2-yl 23701H-1,2,4- 3,4-Me₂—C₆H₃ Me Triazol-2-yl 2371 1H-1,2,4- 2,4-Me₂—C₆H₃ MeTriazol-2-yl 2372 1H-1,2,4- 3-Ph—C₆H₄ Me Triazol-2-yl 2373 1H-1,2,4-4-Ph—C₆H₄ Me Triazol-2-yl 2374 1H-1,2,4- Morpholino Me Triazol-2-yl 23751H-1,2,4- 2,6-Me₂-morpholino Me Triazol-2-yl 2376 1H-1,2,4- C₆H₅ MeTriazol-2-yl 2377 1H-1,2,4- 4-F—C₆H₄ Me Triazol-2-yl 2378 1H-1,2,4-4-Cl—C₆H₄ Me Triazol-2-yl 2379 1H-1,2,4- 4-Me—C₆H₄ Me Triazol-2-yl 23801H-1,2,4- 3,4-Cl₂—C₆H₃ Me Triazol-2-yl 2381 Isoxazol-3-yl C₆H₅ Me 2382Isoxazol-3-yl 2-F—C₆H₄ Me 2383 Isoxazol-3-yl 3-F—C₆H₄ Me 2384Isoxazol-3-yl 4-F—C₆H₄ Me 2385 Isoxazol-3-yl 2-Cl—C₆H₄ Me 2386Isoxazol-3-yl 3-Cl—C₆H₄ Me 2387 Isoxazol-3-yl 4-Cl—C₆H₄ Me¹H-NMR(CDCl₃δppm: 2.04(3H, s), 4.00(3H, s), 5.13(2H, s), 6.74(1H, d,J=1.7), 7.25-7.55(8H, m), 8.36(1H, d, J=1.7) 2388 Isoxazol-3-yl2-Br—C₆H₄ Me 2389 Isoxazol-3-yl 3-Br—C₆H₄ Me 2390 Isoxazol-3-yl4-Br—C₆H₄ Me 2391 Isoxazol-3-yl 3-I—C₆H₄ Me 2392 Isoxazol-3-yl 2-Me—C₆H₄Me 2393 Isoxazol-3-yl 3-Me—C₆H₄ Me 2394 Isoxazol-3-yl 4-Me—C₆H₄ Me¹H-NMR(CDCl₃)δppm: 2.05(3H, s), 2.34(3H, s), 4.00(3H, s), 5.13(2H, s),6.73(1H, d, J=1.7), 7.11- 7.57(8H, m), 8.35(1H, d, J=1.7) 2395Isoxazol-3-yl 3-Et—C₆H₄ Me 2396 Isoxazol-3-yl 4-Et—C₆H₄ Me 2397Isoxazol-3-yl 3-MeO—C₆H₄ Me 2398 Isoxazol-3-yl 4-MeO—C₆H₄ Me¹H-NMR(CDCl₃)δppm: 2.05(3H, s), 3.81(3H, s), 4.00(3H, s), 5.12(2H, s),6.73(1H, d, J=1.7), 6.82- 6.86(2H, m), 7.25-7.56(6H, m), 8.35(1H, d,J=1.7) 2399 Isoxazol-3-yl 3-CF₃—C₆H₄ Me ¹H-NMR(CDCl₃)δppm: 2.07(3H, s),4.00(3H, s), 5.17(2H, s), 6.74(1H, d, J=1.7) 7.26-7.74(7H, m), 7.82(1H,s), 8.36(1H, d, J=1.7) 2400 Isoxazol-3-yl 4-CF₃—C₆H₄ Me¹H-NMR(CDCl₃)δppm: 2.07(3H, s), 4.00(3H, s), 5.16(2H, s), 6.74(1H, d,J=1.8), 7.26-7.67(8H, m), 8.36(1H, d, J=1.8) 2401 Isoxazol-3-yl2,4-F₂—C₆H₃ Me 2402 Isoxazol-3-yl 2,5-F₂—C₆H₃ Me 2403 Isoxazol-3-yl3,4-F₂—C₆H₃ Me 2404 Isoxazol-3-yl 3,5-F₂—C₆H₃ Me 2405 Isoxazol-3-yl2,3-Cl₂—C₆H₃ Me 2406 Isoxazol-3-yl 2,4-Cl₂—C₆H₃ Me 2407 Isoxazol-3-yl2,5-Cl₂—C₆H₃ Me 2408 Isoxazol-3-yl 3,4-Cl₂—C₆H₃ Me ¹H-NMR(CDCl₃)δppm:2.01(3H, s), 4.00(3H, s), 5.14(2H, s), 6.75(1H, d, J=1.7), 7.25-7.65(7H,m), 8.36(1H, d, J=.17) 2409 Isoxazol-3-yl 3,5-Cl₂—C₆H₃ Me 2410Isoxazol-3-yl 3,4-Me₂—C₆H₃ Me 2411 Isoxazol-3-yl 2,4-Me₂—C₆H₃ Me 2412Isoxazol-3-yl 3-Ph—C₆H₄ Me 2413 Isoxazol-3-yl 4-Ph—C₆H₄ Me 2414Isoxazol-3-yl Morpholino Me 2415 Isoxazol-3-yl 2,6-Me₂-morpholino Me2416 Isoxazol-3-yl C₆H₅ Me 2417 Isoxazol-3-yl 4-F—C₆H₄ Me 2418Isoxazol-3-yl 4-Cl—C₆H₄ Me 2419 Isoxazol-3-yl 4-Me—C₆H₄ Me 2420Isoxazol-3-yl 3,4-Cl₂—C₆H₃ Me 2421 5-Me-isoxazol-3-yl C₆H₅ Me 24225-Me-isoxazol-3-yl 2-F—C₆H₄ Me 2423 5-Me-isoxazol-3-yl 3-F—C₆H₄ Me 24245-Me-isoxazol-3-yl 4-F—C₆H₄ Me 2425 5-Me-isoxazol-3-yl 2-Cl—C₆H₄ Me 24265-Me-isoxazol-3-yl 3-Cl—C₆H₄ Me 2427 5-Me-isoxazol-3-yl 4-Cl—C₆H₄ Me2428 5-Me-isoxazol-3-yl 2-Br—C₆H₄ Me 2429 5-Me-isoxazol-3-yl 3-Br—C₆H₄Me 2430 5-Me-isoxazol-3-yl 4-Br—C₆H₄ Me 2431 5-Me-isoxazol-3-yl 3-I—C₆H₄Me 2432 5-Me-isoxazol-3-yl 2-Me—C₆H₄ Me 2433 5-Me-isoxazol-3-yl3-Me—C₆H₄ Me 2434 5-Me-isoxazol-3-yl 4-Me—C₆H₄ Me 24355-Me-isoxazol-3-yl 3-Et—C₆H₄ Me 2436 5-Me-isoxazol-3-yl 4-Et—C₆H₄ Me2437 5-Me-isoxazol-3-yl 3-MeO—C₆H₄ Me 2438 5-Me-isoxazol-3-yl 4-MeO—C₆H₄Me 2439 5-Me-isoxazol-3-yl 3-CF₃—C₆H₄ Me ¹H-NMR(CDCl₃)δppm: 2.11(3H, s),2.40(3H, s) 3.98(3H, s), 5.17(2H, s), 6.35(1H, d, J=0.7), 7.24-7.76(7H,m), 7.83(1H, s) 2440 5-Me-isoxazol-3-yl 4-CF₃—C₆H₄ Me 24415-Me-isoxazol-3-yl 2,4-F₂—C₆H₃ Me 2442 5-Me-isoxazol-3-yl 2,5-F₂—C₆H₃ Me2443 5-Me-isoxazol-3-yl 3,4-F₂—C₆H₃ Me 2444 5-Me-isoxazol-3-yl3,5-F₂—C₆H₃ Me 2445 5-Me-isoxazol-3-yl 2,3-Cl₂—C₆H₃ Me 24465-Me-isoxazol-3-yl 2,4-Cl₂—C₆H₃ Me 2447 5-Me-isoxazol-3-yl 2,5-Cl₂—C₆H₃Me 2448 5-Me-isoxazol-3-yl 3,4-Cl₂—C₆H₃ Me ¹H-NMR(CDCl₃)δppm: 2.05(3H,s), 2.47(3H, s)3.98(3H, s), 5.14(2H, s), 6.35(1H, s), 7.23-7.53(6H, m),7.66(1H, d, J=1.7) 2449 5-Me-isoxazol-3-yl 3,5-Cl₂—C₆H₃ Me 24505-Me-isoxazol-3-yl 3,4-Me₂—C₆H₃ Me 2451 5-Me-isoxazol-3-yl 2,4-Me₂—C₆H₃Me 2452 5-Me-isoxazol-3-yl 3-Ph—C₆H₄ Me 2453 5-Me-isoxazol-3-yl4-Ph—C₆H₄ Me 2454 5-Me-isoxazol-3-yl Morpholino Me 24555-Me-isoxazol-3-yl 2,6-Me₂-morpholino Me 2456 5-Me-isoxazol-3-yl C₆H₅ Me2457 5-Me-isoxazol-3-yl 4-F—C₆H₄ Me 2458 5-Me-isoxazol-3-yl 4-Cl—C₆H₄ Me2459 5-Me-isoxazol-3-yl 4-Me—C₆H₄ Me 2460 5-Me-isoxazol-3-yl3,4-Cl₂—C₆H₃ Me 2461 Isoxazol-5-yl C₆H₅ Me 2462 Isoxazol-5-yl 2-F—C₆H₄Me 2463 Isoxazol-5-yl 3-F—C₆H₄ Me 2464 Isoxazol-5-yl 4-F—C₆H₄ Me 2465Isoxazol-5-yl 2-Cl—C₆H₄ Me 2466 Isoxazol-5-yl 3-Cl—C₆H₄ Me 2467Isoxazol-5-yl 4-Cl—C₆H₄ Me 2468 Isoxazol-5-yl 2-Br—C₆H₄ Me 2469Isoxazol-5-yl 3-Br—C₆H₄ Me 2470 Isoxazol-5-yl 4-Br—C₆H₄ Me 2471Isoxazol-5-yl 3-I—C₆H₄ Me 2472 Isoxazol-5-yl 2-Me—C₆H₄ Me 2473Isoxazol-5-yl 3-Me—C₆H₄ Me 2474 Isoxazol-5-yl 4-Me—C₆H₄ Me 2475Isoxazol-5-yl 3-Et—C₆H₄ Me 2476 Isoxazol-5-yl 4-Et—C₆H₄ Me 2477Isoxazol-5-yl 3-MeO—C₆H₄ Me 2478 Isoxazol-5-yl 4-MeO—C₆H₄ Me 2479Isoxazol-5-yl 3-CF₃—C₆H₄ Me 2480 Isoxazol-5-yl 4-CF₃—C₆H₄ Me 2481Isoxazol-5-yl 2,4-F₂—C₆H₃ Me 2482 Isoxazol-5-yl 2,5-F₂—C₆H₃ Me 2483Isoxazol-5-yl 3,4-F₂—C₆H₃ Me 2484 Isoxazol-5-yl 3,5-F₂—C₆H₃ Me 2485Isoxazol-5-yl 2,3-Cl₂—C₆H₃ Me 2486 Isoxazol-5-yl 2,4-Cl₂—C₆H₃ Me 2487Isoxazol-5-yl 2,5-Cl₂—C₆H₃ Me 2488 Isoxazol-5-yl 3,4-Cl₂—C₆H₃ Me 2489Isoxazol-5-yl 3,5-Cl₂—C₆H₃ Me 2490 Isoxazol-5-yl 3,4-Me₂—C₆H₃ Me 2491Isoxazol-5-yl 2,4-Me₂—C₆H₃ Me 2492 Isoxazol-5-yl 3-Ph—C₆H₄ Me 2493Isoxazol-5-yl 4-Ph—C₆H₄ Me 2494 Isoxazol-5-yl Morpholino Me 2495Isoxazol-5-yl 2,6-Me₂-morpholino Me 2496 Isoxazol-5-yl C₆H₅ Me 2497Isoxazol-5-yl 4-F—C₆H₄ Me 2498 Isoxazol-5-yl 4-Cl—C₆H₄ Me 2499Isoxazol-5-yl 4-Me—C₆H₄ Me 2500 Isoxazol-5-yl 3,4-Cl₂—C₆H₃ Me 25013-Me-isoxazol-5-yl C₆H₅ Me 2502 3-Me-isoxazol-5-yl 2-F—C₆H₄ Me 25033-Me-isoxazol-5-yl 3-F—C₆H₄ Me 2504 3-Me-isoxazol-5-yl 4-F—C₆H₄ Me 25053-Me-isoxazol-5-yl 2-Cl—C₆H₄ Me 2506 3-Me-isoxazol-5-yl 3-Cl—C₆H₄ Me2507 3-Me-isoxazol-5-yl 4-Cl—C₆H₄ Me ¹H-NMR(CDCl₃)δppm: 2.03(3H, S),2.19(3H, S), 4.03(3H, S), 5.12(2H, S), 5.94(2H, S), 7.19-7.56(8H, m)2508 3-Me-isoxazol-5-yl 2-Br—C₆H₄ Me 2509 3-Me-isoxazol-5-yl 3-Br—C₆H₄Me 2510 3-Me-isoxazol-5-yl 4-Br—C₆H₄ Me 2511 3-Me-isoxazol-5-yl 3-I—C₆H₄Me 2512 3-Me-isoxazol-5-yl 2-Me—C₆H₄ Me 2513 3-Me-isoxazol-5-yl3-Me—C₆H₄ Me 2514 3-Me-isoxazol-5-yl 4-Me—C₆H₄ Me 25153-Me-isoxazol-5-yl 3-Et—C₆H₄ Me 2516 3-Me-isoxazol-5-yl 4-Et—C₆H₄ Me2517 3-Me-isoxazol-5-yl 3-MeO—C₆H₄ Me 2518 3-Me-isoxazol-5-yl 4-MeO—C₆H₄Me 2519 3-Me-isoxazol-5-yl 3-CF₃—C₆H₄ Me 2520 3-Me-isoxazol-5-yl4-CF₃—C₆H₄ Me 2521 3-Me-isoxazol-5-yl 2,4-F₂—C₆H₃ Me 25223-Me-isoxazol-5-yl 2,5-F₂—C₆H₃ Me 2523 3-Me-isoxazol-5-yl 3,4-F₂—C₆H₃ Me2524 3-Me-isoxazol-5-yl 3,5-F₂—C₆H₃ Me 2525 3-Me-isoxazol-5-yl2,3-Cl₂—C₆H₃ Me 2526 3-Me-isoxazol-5-yl 2,4-Cl₂—C₆H₃ Me 25273-Me-isoxazol-5-yl 2,5-Cl₂—C₆H₃ Me 2528 3-Me-isoxazol-5-yl 3,4-Cl₂—C₆H₃Me mp 84.0-85.0° C. 2529 3-Me-isoxazol-5-yl 3,5-Cl₂—C₆H₃ Me 25303-Me-isoxazol-5-yl 3,4-Me₂—C₆H₃ Me 2531 3-Me-isoxazol-5-yl 2,4-Me₂—C₆H₃Me 2532 3-Me-isoxazol-5-yl 3-Ph—C₆H₄ Me 2533 3-Me-isoxazol-5-yl4-Ph—C₆H₄ Me 2534 3-Me-isoxazol-5-yl Morpholino Me 25353-Me-isoxazol-5-yl 2,6-Me₂-morpholino Me 2536 3-Me-isoxazol-5-yl C₆H₅ Et2537 3-Me-isoxazol-5-yl 4-F—C₆H₄ Et 2538 3-Me-isoxazol-5-yl 4-Cl—C₆H₄ Et2539 3-Me-isoxazol-5-yl 4-Me—C₆H₄ Et 2540 3-Me-isoxazol-5-yl3,4-Cl₂—C₆H₃ Et 2541 1,3,4-Oxadiazol-2-yl C₆H₅ Me 25421,3,4-Oxadiazol-2-yl 2-F—C₆H₄ Me 2543 1,3,4-Oxadiazol-2-yl 3-F—C₆H₄ Me2544 1,3,4-Oxadiazol-2-yl 4-F—C₆H₄ Me 2545 1,3,4-Oxadiazol-2-yl2-Cl—C₆H₄ Me 2546 1,3,4-Oxadiazol-2-yl 3-Cl—C₆H₄ Me 25471,3,4-Oxadiazol-2-yl 4-Cl—C₆H₄ Me 2548 1,3,4-Oxadiazol-2-yl 2-Br—C₆H₄ Me2549 1,3,4-Oxadiazol-2-yl 3-Br—C₆H₄ Me 2550 1,3,4-Oxadiazol-2-yl4-Br—C₆H₄ Me 2551 1,3,4-Oxadiazol-2-yl 3-I—C₆H₄ Me 25521,3,4-Oxadiazol-2-yl 2-Me—C₆H₄ Me 2553 1,3,4-Oxadiazol-2-yl 3-Me—C₆H₄ Me2554 1,3,4-Oxadiazol-2-yl 4-Me—C₆H₄ Me 2555 1,3,4-Oxadiazol-2-yl3-Et—C₆H₄ Me 2556 1,3,4-Oxadiazol-2-yl 4-Et—C₆H₄ Me 25571,3,4-Oxadiazol-2-yl 3-MeO—C₆H₄ Me 2558 1,3,4-Oxadiazol-2-yl 4-MeO—C₆H₄Me 2559 1,3,4-Oxadiazol-2-yl 3-CF₃—C₆H₄ Me 2560 1,3,4-Oxadiazol-2-yl4-CF₃—C₆H₄ Me 2561 1,3,4-Oxadiazol-2-yl 2,4-F₂—C₆H₃ Me 25621,3,4-Oxadiazol-2-yl 2,5-F₂—C₆H₃ Me 2563 1,3,4-Oxadiazol-2-yl3,4-F₂—C₆H₃ Me 2564 1,3,4-Oxadiazol-2-yl 3,5-F₂—C₆H₃ Me 25651,3,4-Oxadiazol-2-yl 2,3-Cl₂—C₆H₃ Me 2566 1,3,4-Oxadiazol-2-yl2,4-Cl₂—C₆H₃ Me 2567 1,3,4-Oxadiazol-2-yl 2,5-Cl₂—C₆H₃ Me 25681,3,4-Oxadiazol-2-yl 3,4-Cl₂—C₆H₃ Me 2569 1,3,4-Oxadiazol-2-yl3,5-Cl₂—C₆H₃ Me 2570 1,3,4-Oxadiazol-2-yl 3,4-Me₂—C₆H₃ Me 25711,3,4-Oxadiazol-2-yl 2,4-Me₂—C₆H₃ Me 2572 1,3,4-Oxadiazol-2-yl 3-Ph—C₆H₄Me 2573 1,3,4-Oxadiazol-2-yl 4-Ph—C₆H₄ Me 2574 1,3,4-Oxadiazol-2-ylMorpholino Me 2575 1,3,4-Oxadiazol-2-yl 2,6-Me₂-morpholino Me 25761,3,4-Oxadiazol-2-yl C₆H₅ Me 2577 1,3,4-Oxadiazol-2-yl 4-F—C₆H₄ Me 25781,3,4-Oxadiazol-2-yl 4-Cl—C₆H₄ Me 2579 1,3,4-Oxadiazol-2-yl 4-Me—C₆H₄ Me2580 1,3,4-Oxadiazol-2-yl 3,4-Cl₂—C₆H₃ Me 2581 5-Me-1,3,4- C₆H₅ Meoxadiazol-2-yl 2582 5-Me-1,3,4- 2-F—C₆H₄ Me oxadiazol-2-yl 25835-Me-1,3,4- 3-F—C₆H₄ Me oxadiazol-2-yl 2584 5-Me-1,3,4- 4-F—C₆H₄ Meoxadiazol-2-yl 2585 5-Me-1,3,4- 2-Cl—C₆H₄ Me oxadiazol-2-yl 25865-Me-1,3,4- 3-Cl—C₆H₄ Me oxadiazol-2-yl 2587 5-Me-1,3,4- 4-Cl—C₆H₄ Meoxadiazol-2-yl 2588 5-Me-1,3,4- 2-Br—C₆H₄ Me oxadiazol-2-yl 25895-Me-1,3,4- 3-Br—C₆H₄ Me oxadiazol-2-yl 2590 5-Me-1,3,4- 4-Br—C₆H₄ Meoxadiazol-2-yl 2591 5-Me-1,3,4- 3-I—C₆H₄ Me oxadiazol-2-yl 25925-Me-1,3,4- 2-Me—C₆H₄ Me oxadiazol-2-yl 2593 5-Me-1,3,4- 3-Me—C₆H₄ Meoxadiazol-2-yl 2594 5-Me-1,3,4- 4-Me—C₆H₄ Me oxadiazol-2-yl 25955-Me-1,3,4- 3-Et—C₆H₄ Me oxadiazol-2-yl 2596 5-Me-1,3,4- 4-Et—C₆H₄ Meoxadiazol-2-yl 2597 5-Me-1,3,4- 3-MeO—C₆H₄ Me oxadiazol-2-yl 25985-Me-1,3,4- 4-MeO—C₆H₄ Me oxadiazol-2-yl 2599 5-Me-1,3,4- 3-CF₃—C₆H₄ Meoxadiazol-2-yl 2600 5-Me-1,3,4- 4-CF₃—C₆H₄ Me oxadiazol-2-yl 26015-Me-1,3,4- 2,4-F₂—C₆H₃ Me oxadiazol-2-yl 2602 5-Me-1,3,4- 2,5-F₂—C₆H₃Me oxadiazol-2-yl 2603 5-Me-1,3,4- 3,4-F₂—C₆H₃ Me oxadiazol-2-yl 26045-Me-1,3,4- 3,5-F₂—C₆H₃ Me oxadiazol-2-yl 2605 5-Me-1,3,4- 2,3-Cl₂—C₆H₃Me oxadiazol-2-yl 2606 5-Me-1,3,4- 2,4-Cl₂—C₆H₃ Me oxadiazol-2-yl 26075-Me-1,3,4- 2,5-Cl₂—C₆H₃ Me oxadiazol-2-yl 2608 5-Me-1,3,4- 3,4-Cl₂—C₆H₃Me oxadiazol-2-yl 2609 5-Me-1,3,4- 3,5-Cl₂—C₆H₃ Me oxadiazol-2-yl 26105-Me-1,3,4- 3,4-Me₂—C₆H₃ Me oxadiazol-2-yl 2611 5-Me-1,3,4- 2,4-Me₂—C₆H₃Me oxadiazol-2-yl 2612 5-Me-1,3,4- 3-Ph—C₆H₄ Me oxadiazol-2-yl 26135-Me-1,3,4- 4-Ph—C₆H₄ Me oxadiazol-2-yl 2614 5-Me-1,3,4- Morpholino Meoxadiazol-2-yl 2615 5-Me-1,3,4- 2,6-Me₂-morpholino Me oxadiazol-2-yl2616 5-Me-1,3,4- C₆H₅ Et oxadiazol-2-yl 2617 5-Me-1,3,4- 4-F—C₆H₄ Etoxadiazol-2-yl 2618 5-Me-1,3,4- 4-Cl—C₆H₄ Et oxadiazol-2-yl 26195-Me-1,3,4- 4-Me—C₆H₄ Et oxadiazol-2-yl 2620 5-Me-1,3,4- 3,4-Cl₂—C₆H₃ Etoxadiazol-2-yl 2621 Oxazol-5-yl C₆H₅ Me mp 92.0-93.5° C. 2622Oxazol-5-yl 2-F—C₆H₄ Me 2623 Oxazol-5-yl 3-F—C₆H₄ Me 2624 Oxazol-5-yl4-F—C₆H₄ Me 2625 Oxazol-5-yl 2-Cl—C₆H₄ Me 2626 Oxazol-5-yl 3-Cl—C₆H₄ Me2627 Oxazol-5-yl 4-Cl—C₆H₄ Me ¹H-NMR(CDCl₃)δppm: 2.02(3H, S), 4.01(3H,S), 5.14(2H, S), 6.82(1H, S), 7.21-7.58(8H, m), 7.90(1H, S) 2628Oxazol-5-yl 2-Br—C₆H₄ Me 2629 Oxazol-5-yl 3-Br—C₆H₄ Me 2630 Oxazol-5-yl4-Br—C₆H₄ Me 2631 Oxazol-5-yl 3-I—C₆H₄ Me 2632 Oxazol-5-yl 2-Me—C₆H₄ Me2633 Oxazol-5-yl 3-Me—C₆H₄ Me 2634 Oxazol-5-yl 4-Me—C₆H₄ Me 2635Oxazol-5-yl 3-Et—C₆H₄ Me 2636 Oxazol-5-yl 4-Et—C₆H₄ Me 2637 Oxazol-5-yl3-MeO—C₆H₄ Me 2638 Oxazol-5-yl 4-MeO—C₆H₄ Me 2639 Oxazol-5-yl 3-CF₃—C₆H₄Me ¹H-NMR(CDCl₃)δppm: 2.06(3H, S), 4.01(3H, S), 5.17(2H, S), 6.83(1H,S), 7.22-7.26(1H, m), 7.38-7.59(5H, m), 7.72(1H, d, J=7.9), 7.81(1H, S),7.91(1H, S) 2640 Oxazol-5-yl 4-CF₃—C₆H₄ Me 2641 Oxazol-5-yl 2,4-F₂—C₆H₃Me 2642 Oxazol-5-yl 2,5-F₂—C₆H₃ Me 2643 Oxazol-5-yl 3,4-F₂—C₆H₃ Me 2644Oxazol-5-yl 3,5-F₂—C₆H₃ Me 2645 Oxazol-5-yl 2,3-Cl₂—C₆H₃ Me 2646Oxazol-5-yl 2,4-Cl₂—C₆H₃ Me ¹H-NMR(CDCl₃)δppm: 2.02(3H, S), 4.00(3H, S),5.13(2H, S), 6.85(1H, S), 7.13-7.58(7H, m) 7.91(1H, S) 2647 Oxazol-5-yl2,5-Cl₂—C₆H₃ Me 2648 Oxazol-5-yl 3,4-Cl₂—C₆H₃ Me mp 94.0-95.0° C. 2649Oxazol-5-yl 3,5-Cl₂—C₆H₃ Me 2650 Oxazol-5-yl 3,4-Me₂—C₆H₃ Me 2651Oxazol-5-yl 2,4-Me₂—C₆H₃ Me 2652 Oxazol-5-yl 3-Ph—C₆H₄ Me 2653Oxazol-5-yl 4-Ph—C₆H₄ Me 2654 Oxazol-5-yl Morpholino Me 2655 Oxazol-5-yl2,6-Me₂-morpholino Me 2656 Oxazol-5-yl C₆H₅ Et 2657 Oxazol-5-yl 4-F—C₆H₄Et 2658 Oxazol-5-yl 4-Cl—C₆H₄ Et 2659 Oxazol-5-yl 4-Me—C₆H₄ Et 2660Oxazol-5-yl 3,4-Cl₂—C₆H₃ Et 2661 5-Me-1,2,4- C₆H₅ Me ¹H-NMR(CDCl₃)δppm:oxadiazol-3-yl 2.11(3H, s), 2.95(3H, s), 4.08(3H, s), 5.16(2H, s),7.26-7.58(9H, m) 2662 5-Me-1,2,4- 2-F—C₆H₄ Me oxadiazol-3-yl 26635-Me-1,2,4- 3-F—C₆H₄ Me oxadiazol-3-yl 2664 5-Me-1,2,4- 4-F—C₆H₄ Meoxadiazol-3-yl 2665 5-Me-1,2,4- 2-Cl—C₆H₄ Me oxadiazol-3-yl 26665-Me-1,2,4- 3-Cl—C₆H₄ Me oxadiazol-3-yl 2667 5-Me-1,2,4- 4-Cl—C₆H₄ Meoxadiazol-3-yl 2668 5-Me-1,2,4- 2-Br—C₆H₄ Me oxadiazol-3-yl 26695-Me-1,2,4- 3-Br—C₆H₄ Me oxadiazol-3-yl 2670 5-Me-1,2,4- 4-Br—C₆H₄ Meoxadiazol-3-yl 2671 5-Me-1,2,4- 3-I—C₆H₄ Me oxadiazol-3-yl 26725-Me-1,2,4- 2-Me—C₆H₄ Me oxadiazol-3-yl 2673 5-Me-1,2,4- 3-Me—C₆H₄ Meoxadiazol-3-yl 2674 5-Me-1,2,4- 4-Me—C₆H₄ Me oxadiazol-3-yl 26755-Me-1,2,4- 3-Et—C₆H₄ Me oxadiazol-3-yl 2676 5-Me-1,2,4- 4-Et—C₆H₄ Meoxadiazol-3-yl 2677 5-Me-1,2,4- 3-MeO—C₆H₄ Me oxadiazol-3-yl 26785-Me-1,2,4- 4-MeO—C₆H₄ Me oxadiazol-3-yl 2679 5-Me-1,2,4- 3-CF₃—C₆H₄ Meoxadiazol-3-yl 2680 5-Me-1,2,4- 4-CF₃—C₆H₄ Me oxadiazol-3-yl 26815-Me-1,2,4- 2,4-F₂—C₆H₃ Me oxadiazol-3-yl 2682 5-Me-1,2,4- 2,5-F₂—C₆H₃Me oxadiazol-3-yl 2683 5-Me-1,2,4- 3,4-F₂—C₆H₃ Me oxadiazol-3-yl 26845-Me-1,2,4- 3,5-F₂—C₆H₃ Me oxadiazol-3-yl 2685 5-Me-1,2,4- 2,3-Cl₂—C₆H₃Me oxadiazol-3-yl 2686 5-Me-1,2,4- 2,4-Cl₂—C₆H₃ Me oxadiazol-3-yl 26875-Me-1,2,4- 2,5-Cl₂—C₆H₃ Me oxadiazol-3-yl 2688 5-Me-1,2,4- 3,4-Cl₂—C₆H₃Me oxadiazol-3-yl 2689 5-Me-1,2,4- 3,5-Cl₂—C₆H₃ Me oxadiazol-3-yl 26905-Me-1,2,4- 3,4-Me₂—C₆H₃ Me oxadiazol-3-yl 2691 5-Me-1,2,4- 2,4-Me₂—C₆H₃Me oxadiazol-3-yl 2692 5-Me-1,2,4- 3-Ph—C₆H₄ Me oxadiazol-3-yl 26935-Me-1,2,4- 4-Ph—C₆H₄ Me oxadiazol-3-yl 2694 5-Me-1,2,4- Morpholino Meoxadiazol-3-yl 2695 5-Me-1,2,4- 2,6-Me₂-morpholino Me oxadiazol-3-yl2696 5-Me-1,2,4- C₆H₅ Me oxadiazol-3-yl 2697 5-Me-1,2,4- 4-F—C₆H₄ Meoxadiazol-3-yl 2698 5-Me-1,2,4- 4-Cl—C₆H₄ Me oxadiazol-3-yl 26995-Me-1,2,4- 4-Me—C₆H₄ Me oxadiazol-3-yl 2700 5-Me-1,2,4- 3,4-Cl₂—C₆H₃ Meoxadiazol-3-yl 2701 1-Me-1H- C₆H₅ Me mp 119-120° C. tetrazol-5-yl 27021-Me-1H- 2-F—C₆H₄ Me tetrazol-5-yl 2703 1-Me-1H- 3-F—C₆H₄ Metetrazol-5-yl 2704 1-Me-1H- 4-F—C₆H₄ Me tetrazol-5-yl 2705 1-Me-1H-2-Cl—C₆H₄ Me tetrazol-5-yl 2706 1-Me-1H- 3-Cl—C₆H₄ Me tetrazol-5-yl 27071-Me-1H- 4-Cl—C₆H₄ Me tetrazol-5-yl 2708 1-Me-1H- 2-Br—C₆H₄ Metetrazol-5-yl 2709 1-Me-1H- 3-Br—C₆H₄ Me tetrazol-5-yl 2710 1-Me-1H-4-Br—C₆H₄ Me tetrazol-5-yl 2711 1-Me-1H- 3-I—C₆H₄ Me tetrazol-5-yl 27121-Me-1H- 2-Me—C₆H₄ Me tetrazol-5-yl 2713 1-Me-1H- 3-Me—C₆H₄ Metetrazol-5-yl 2714 1-Me-1H- 4-Me—C₆H₄ Me tetrazol-5-yl 2715 1-Me-1H-3-Et—C₆H₄ Me tetrazol-5-yl 2716 1-Me-1H- 4-Et—C₆H₄ Me tetrazol-5-yl 27171-Me-1H- 3-MeO—C₆H₄ Me tetrazol-5-yl 2718 1-Me-1H- 4-MeO—C₆H₄ Metetrazol-5-yl 2719 1-Me-1H- 3-CF₃—C₆H₄ Me tetrazol-5-yl 2720 1-Me-1H-4-CF₃—C₆H₄ Me tetrazol-5-yl 2721 1-Me-1H- 2,4-F₂—C₆H₃ Me tetrazol-5-yl2722 1-Me-1H- 2,5-F₂—C₆H₃ Me tetrazol-5-yl 2723 1-Me-1H- 3,4-F₂—C₆H₃ Metetrazol-5-yl 2724 1-Me-1H- 3,5-F₂—C₆H₃ Me tetrazol-5-yl 2725 1-Me-1H-2,3-Cl₂—C₆H₃ Me tetrazol-5-yl 2726 1-Me-1H- 2,4-Cl₂—C₆H₃ Metetrazol-5-yl 2727 1-Me-1H- 2,5-Cl₂—C₆H₃ Me tetrazol-5-yl 2728 1-Me-1H-3,4-Cl₂—C₆H₃ Me tetrazol-5-yl 2729 1-Me-1H- 3,5-Cl₂—C₆H₃ Metetrazol-5-yl 2730 1-Me-1H- 3,4-Me₂—C₆H₃ Me tetrazol-5-yl 2731 1-Me-1H-2,4-Me₂—C₆H₃ Me tetrazol-5-yl 2732 1-Me-1H- 3-Ph—C₆H₄ Me tetrazol-5-yl2733 1-Me-1H- 4-Ph—C₆H₄ Me tetrazol-5-yl 2734 1-Me-1H- morpholino Metetrazol-5-yl 2735 1-Me-1H- 2,6-Me₂-morpholino Me tetrazol-5-yl 27361-Me-1H- C₆H₅ Et tetrazol-5-yl 2737 1-Me-1H- 4-F—C₆H₄ Et tetrazol-5-yl2738 1-Me-1H- 4-Cl—C₆H₄ Et tetrazol-5-yl 2739 1-Me-1H- 4-Me—C₆H₄ Ettetrazol-5-yl 2740 1-Me-1H- 3,4-Cl₂—C₆H₃ Et tetrazol-5-yl 2741 2-Me-2H-C₆H₅ Me mp 96-98° C. tetrazol-5-yl 2742 2-Me-2H- 2-F—C₆H₄ Metetrazol-5-yl 2743 2-Me-2H- 3-F—C₆H₄ Me tetrazol-5-yl 2744 2-Me-2H-4-F—C₆H₄ Me tetrazol-5-yl 2745 2-Me-2H- 2-Cl—C₆H₄ Me tetrazol-5-yl 27462-Me-2H- 3-Cl—C₆H₄ Me tetrazol-5-yl 2747 2-Me-2H- 4-Cl—C₆H₄ Metetrazol-5-yl 2748 2-Me-2H- 2-Br—C₆H₄ Me tetrazol-5-yl 2749 2-Me-2H-3-Br—C₆H₄ Me tetrazol-5-yl 2750 2-Me-2H- 4-Br—C₆H₄ Me tetrazol-5-yl 27512-Me-2H- 3-I—C₆H₄ Me tetrazol-5-yl 2752 2-Me-2H- 2-Me—C₆H₄ Metetrazol-5-yl 2753 2-Me-2H- 3-Me—C₆H₄ Me tetrazol-5-yl 2754 2-Me-2H-4-Me—C₆H₄ Me tetrazol-5-yl 2755 2-Me-2H- 3-Et—C₆H₄ Me tetrazol-5-yl 27562-Me-2H- 4-Et—C₆H₄ Me tetrazol-5-yl 2757 2-Me-2H- 3-MeO—C₆H₄ Metetrazol-5-yl 2758 2-Me-2H- 4-MeO—C₆H₄ Me tetrazol-5-yl 2759 2-Me-2H-3-CF₃—C₆H₄ Me tetrazol-5-yl 2760 2-Me-2H- 4-CF₃—C₆H₄ Me tetrazol-5-yl2761 2-Me-2H- 2,4-F₂—C₆H₃ Me tetrazol-5-yl 2762 2-Me-2H- 2,5-F₂—C₆H₃ Metetrazol-5-yl 2763 2-Me-2H- 3,4-F₂—C₆H₃ Me tetrazol-5-yl 2764 2-Me-2H-3,5-F₂—C₆H₃ Me tetrazol-5-yl 2765 2-Me-2H- 2,3-Cl₂—C₆H₃ Me tetrazol-5-yl2766 2-Me-2H- 2,4-Cl₂—C₆H₃ Me tetrazol-5-yl 2767 2-Me-2H- 2,5-Cl₂—C₆H₃Me tetrazol-5-yl 2768 2-Me-2H- 3,4-Cl₂—C₆H₃ Me tetrazol-5-yl 27692-Me-2H- 3,5-Cl₂—C₆H₃ Me tetrazol-5-yl 2770 2-Me-2H- 3,4-Me₂—C₆H₃ Metetrazol-5-yl 2771 2-Me-2H- 2,4-Me₂—C₆H₃ Me tetrazol-5-yl 2772 2-Me-2H-3-Ph—C₆H₄ Me tetrazol-5-yl 2773 2-Me-2H- 4-Ph—C₆H₄ Me tetrazol-5-yl 27742-Me-2H- Morpholino Me tetrazol-5-yl 2775 2-Me-2H- 2,6-Me₂-morpholino Metetrazol-5-yl 2776 2-Me-2H- C₆H₅ Et tetrazol-5-yl 2777 2-Me-2H- 4-F—C₆H₄Et tetrazol-5-yl 2778 2-Me-2H- 4-Cl—C₆H₄ Et tetrazol-5-yl 2779 2-Me-2H-4-Me—C₆H₄ Et tetrazol-5-yl 2780 2-Me-2H- 3,4-Cl₂—C₆H₃ Et tetrazol-5-yl2781 Thiazolidin-2-yl C₆H₅ Me 2782 Thiazolidin-2-yl 2-F—C₆H₄ Me 2783Thiazolidin-2-yl 3-F—C₆H₄ Me 2784 Thiazolidin-2-yl 4-F—C₆H₄ Me 2785Thiazolidin-2-yl 2-Cl—C₆H₄ Me 2786 Thiazolidin-2-yl 3-Cl—C₆H₄ Me 2787Thiazolidin-2-yl 4-Cl—C₆H₄ Me 2788 Thiazolidin-2-yl 2-Br—C₆H₄ Me 2789Thiazolidin-2-yl 3-Br—C₆H₄ Me 2790 Thiazolidin-2-yl 4-Br—C₆H₄ Me 2791Thiazolidin-2-yl 3-I—C₆H₄ Me 2792 Thiazolidin-2-yl 2-Me—C₆H₄ Me 2793Thiazolidin-2-yl 3-Me—C₆H₄ Me 2794 Thiazolidin-2-yl 4-Me—C₆H₄ Me 2795Thiazolidin-2-yl 3-Et—C₆H₄ Me 2796 Thiazolidin-2-yl 4-Et—C₆H₄ Me 2797Thiazolidin-2-yl 3-MeO—C₆H₄ Me 2798 Thiazolidin-2-yl 4-MeO—C₆H₄ Me 2799Thiazolidin-2-yl 3-CF₃—C₆H₄ Me ¹H-NMR(CDCl₃)δppm: 2.39(3H, S),2.75-3.10(3H, m) 3.50(2H, m), 3.86(3H, S), 5.20-5.30(2H, m),5.30-5.50(1H, m), 7.37-7.61(6H, m), 7.82(1H, j=7.9), 7.91(1H, S) 2800Thiazolidin-2-yl 4-CF₃—C₆H₄ Me 2801 Thiazolidin-2-yl 2,4-F₂—C₆H₃ Me 2802Thiazolidin-2-yl 2,5-F₂—C₆H₃ Me 2803 Thiazolidin-2-yl 3,4-F₂—C₆H₃ Me2804 Thiazolidin-2-yl 3,5-F₂—C₆H₃ Me 2805 Thiazolidin-2-yl 2,3-Cl₂—C₆H₃Me 2806 Thiazolidin-2-yl 2,4-Cl₂—C₆H₃ Me 2807 Thiazolidin-2-yl2,5-Cl₂—C₆H₃ Me 2808 Thiazolidin-2-yl 3,4-Cl₂—C₆H₃ Me 2809Thiazolidin-2-yl 3,5-Cl₂—C₆H₃ Me 2810 Thiazolidin-2-yl 3,4-Me₂—C₆H₃ Me2811 Thiazolidin-2-yl 2,4-Me₂—C₆H₃ Me 2812 Thiazolidin-2-yl 3-Ph—C₆H₄ Me2813 Thiazolidin-2-yl 4-Ph—C₆H₄ Me 2814 Thiazolidin-2-yl Morpholino Me¹H-NMR(CDCl₃)δppm: 1.98(3H, S), 2.70-2.80(1H, m), 2.89-3.06(2H, m),3.10(4H, t j=4.9), 3.4-3.5(2H, m), 3.69(4H, t j=4.9), 3.83(3H, S),4.91(2H, S), 5.40(1H, S)7.33-7.55(4H, m) 2815 Thiazolidin-2-yl2,6-Me₂-morpholino Me 2816 Thiazolidin-2-yl C₆H₅ Me 2817Thiazolidin-2-yl 4-F—C₆H₄ Me 2818 Thiazolidin-2-yl 4-Cl—C₆H₄ Me 2819Thiazolidin-2-yl 4-Me—C₆H₄ Me 2820 Thiazolidin-2-yl 3,4-Cl₂—C₆H₃ Me 28213-Me-thiazolidin-2-yl C₆H₅ Me 2822 3-Me-thiazolidin-2-yl 2-F—C₆H₄ Me2823 3-Me-thiazolidin-2-yl 3-F—C₆H₄ Me 2824 3-Me-thiazolidin-2-yl4-F—C₆H₄ Me 2825 3-Me-thiazolidin-2-yl 2-Cl—C₆H₄ Me 28263-Me-thiazolidin-2-yl 3-Cl—C₆H₄ Me 2827 3-Me-thiazolidin-2-yl 4-Cl—C₆H₄Me 2828 3-Me-thiazolidin-2-yl 2-Br—C₆H₄ Me 2829 3-Me-thiazolidin-2-yl3-Br—C₆H₄ Me 2830 3-Me-thiazolidin-2-yl 4-Br—C₆H₄ Me 28313-Me-thiazolidin-2-yl 3-I—C₆H₄ Me 2832 3-Me-thiazolidin-2-yl 2-Me—C₆H₄Me 2833 3-Me-thiazolidin-2-yl 3-Me—C₆H₄ Me 2834 3-Me-thiazolidin-2-yl4-Me—C₆H₄ Me 2835 3-Me-thiazolidin-2-yl 3-Et—C₆H₄ Me 28363-Me-thiazolidin-2-yl 4-Et—C₆H₄ Me 2837 3-Me-thiazolidin-2-yl 3-MeO—C₆H₄Me 2838 3-Me-thiazolidin-2-yl 4-MeO—C₆H₄ Me 2839 3-Me-thiazolidin-2-yl3-CF₃—C₆H₄ Me ¹H-NMR(CDCl₃)δppm: 2.31(3H, d j=3.7), 2.47(3H, d j=14.7),2.83-3.25(4H, m), 3.84(3H, S), 4.94((1H, d j=54.9), 5.14- 5.35(2H, m),7.19-7.60(6H, m), 7.83(1H, d j=7.9), 7.93(1H, S) 28403-Me-thiazolidin-2-yl 4-CF₃—C₆H₄ Me 2841 3-Me-thiazolidin-2-yl2,4-F₂—C₆H₃ Me 2842 3-Me-thiazolidin-2-yl 2,5-F₂—C₆H₃ Me 28433-Me-thiazolidin-2-yl 3,4-F₂—C₆H₃ Me 2844 3-Me-thiazolidin-2-yl3,5-F₂—C₆H₃ Me 2845 3-Me-thiazolidin-2-yl 2,3-Cl₂—C₆H₃ Me 28463-Me-thiazolidin-2-yl 2,4-Cl₂—C₆H₃ Me 2847 3-Me-thiazolidin-2-yl2,5-Cl₂—C₆H₃ Me 2848 3-Me-thiazolidin-2-yl 3,4-Cl₂—C₆H₃ Me 28493-Me-thiazolidin-2-yl 3,5-Cl₂—C₆H₃ Me 2850 3-Me-thiazolidin-2-yl3,4-Me₂—C₆H₃ Me 2851 3-Me-thiazolidin-2-yl 2,4-Me₂—C₆H₃ Me 28523-Me-thiazolidin-2-yl 3-Ph—C₆H₄ Me 2853 3-Me-thiazolidin-2-yl 4-Ph—C₆H₄Me 2854 3-Me-thiazolidin-2-yl Morpholino Me 2855 3-Me-thiazolidin-2-yl2,6-Me₂-morpholino Me 2856 3-Me-thiazolidin-2-yl C₆H₅ Et 28573-Me-thiazolidin-2-yl 4-F—C₆H₄ Et 2858 3-Me-thiazolidin-2-yl 4-Cl—C₆H₄Et 2859 3-Me-thiazolidin-2-yl 4-Me—C₆H₄ Et 2860 3-Me-thiazolidin-2-yl3,4-Cl₂—C₆H₃ Et 2861 2-Isoxazolin-3-yl C₆H₅ Me 2862 2-Isoxazolin-3-yl2-F—C₆H₄ Me 2863 2-Isoxazolin-3-yl 3-F—C₆H₄ Me 2864 2-Isoxazolin-3-yl4-F—C₆H₄ Me 2865 2-Isoxazolin-3-yl 2-Cl—C₆H₄ Me 2866 2-Isoxazolin-3-yl3-Cl—C₆H₄ Me 2867 2-Isoxazolin-3-yl 4-Cl—C₆H₄ Me 2868 2-Isoxazolin-3-yl2-Br—C₆H₄ Me 2869 2-Isoxazolin-3-yl 3-Br—C₆H₄ Me 2870 2-Isoxazolin-3-yl4-Br—C₆H₄ Me 2871 2-Isoxazolin-3-yl 3-I—C₆H₄ Me 2872 2-Isoxazolin-3-yl2-Me—C₆H₄ Me 2873 2-Isoxazolin-3-yl 3-Me—C₆H₄ Me 2874 2-Isoxazolin-3-yl4-Me—C₆H₄ Me 2875 2-Isoxazolin-3-yl 3-Et—C₆H₄ Me 2876 2-Isoxazolin-3-yl4-Et—C₆H₄ Me 2877 2-Isoxazolin-3-yl 3-MeO—C₆H₄ Me 2878 2-Isoxazolin-3-yl4-MeO—C₆H₄ Me 2879 2-Isoxazolin-3-yl 3-CF₃—C₆H₄ Me 28802-Isoxazolin-3-yl 4-CF₃—C₆H₄ Me 2881 2-Isoxazolin-3-yl 2,4-F₂—C₆H₃ Me2882 2-Isoxazolin-3-yl 2,5-F₂—C₆H₃ Me 2883 2-Isoxazolin-3-yl 3,4-F₂—C₆H₃Me 2884 2-Isoxazolin-3-yl 3,5-F₂—C₆H₃ Me 2885 2-Isoxazolin-3-yl2,3-Cl₂—C₆H₃ Me 2886 2-Isoxazolin-3-yl 2,4-Cl₂—C₆H₃ Me 28872-Isoxazolin-3-yl 2,5-Cl₂—C₆H₃ Me 2888 2-Isoxazolin-3-yl 3,4-Cl₂—C₆H₃ Me2889 2-Isoxazolin-3-yl 3,5-Cl₂—C₆H₃ Me 2890 2-Isoxazolin-3-yl3,4-Me₂—C₆H₃ Me 2891 2-Isoxazolin-3-yl 2,4-Me₂—C₆H₃ Me 28922-Isoxazolin-3-yl 3-Ph—C₆H₄ Me 2893 2-Isoxazolin-3-yl 4-Ph—C₆H₄ Me 28942-Isoxazolin-3-yl Morpholino Me 2895 2-Isoxazolin-3-yl2,6-Me₂-morpholino Me 2896 2-Isoxazolin-3-yl C₆H₅ Et 28972-Isoxazolin-3-yl 4-F—C₆H₄ Et 2898 2-Isoxazolin-3-yl 4-Cl—C₆H₄ Et 28992-Isoxazolin-3-yl 4-Me—C₆H₄ Et 2900 2-Isoxazolin-3-yl 3,4-Cl₂—C₆H₃ Et2901 5-Me-2- C₆H₅ Me isoxazolin-3-yl 2902 5-Me-2- 2-F—C₆H₄ Meisoxazolin-3-yl 2903 5-Me-2- 3-F—C₆H₄ Me isoxazolin-3-yl 2904 5-Me-2-4-F—C₆H₄ Me isoxazolin-3-yl 2905 5-Me-2- 2-Cl—C₆H₄ Me isoxazolin-3-yl2906 5-Me-2- 3-Cl—C₆H₄ Me isoxazolin-3-yl 2907 5-Me-2- 4-Cl—C₆H₄ Meisoxazolin-3-yl 2908 5-Me-2- 2-Br—C₆H₄ Me isoxazolin-3-yl 2909 5-Me-2-3-Br—C₆H₄ Me isoxazolin-3-yl 2910 5-Me-2- 4-Br—C₆H₄ Me isoxazolin-3-yl2911 5-Me-2- 3-I—C₆H₄ Me isoxazolin-3-yl 2912 5-Me-2- 2-Me—C₆H₄ Meisoxazolin-3-yl 2913 5-Me-2- 3-Me—C₆H₄ Me isoxazolin-3-yl 2914 5-Me-2-4-Me—C₆H₄ Me isoxazolin-3-yl 2915 5-Me-2- 3-Et—C₆H₄ Me isoxazolin-3-yl2916 5-Me-2- 4-Et—C₆H₄ Me isoxazolin-3-yl 2917 5-Me-2- 3-MeO—C₆H₄ Meisoxazolin-3-yl 2918 5-Me-2- 4-MeO—C₆H₄ Me isoxazolin-3-yl 2919 5-Me-2-3-CF₃—C₆H₄ Me isoxazolin-3-yl 2920 5-Me-2- 4-CF₃—C₆H₄ Me isoxazolin-3-yl2921 5-Me-2- 2,4-F₂—C₆H₃ Me isoxazolin-3-yl 2922 5-Me-2- 2,5-F₂—C₆H₃ Meisoxazolin-3-yl 2923 5-Me-2- 3,4-F₂—C₆H₃ Me isoxazolin-3-yl 2924 5-Me-2-3,5-F₂—C₆H₃ Me isoxazolin-3-yl 2925 5-Me-2- 2,3-Cl₂—C₆H₃ Meisoxazolin-3-yl 2926 5-Me-2- 2,4-Cl₂—C₆H₃ Me isoxazolin-3-yl 29275-Me-2- 2,5-Cl₂—C₆H₃ Me isoxazolin-3-yl 2928 5-Me-2- 3,4-Cl₂—C₆H₃ Meisoxazolin-3-yl 2929 5-Me-2- 3,5-Cl₂—C₆H₃ Me isoxazolin-3-yl 29305-Me-2- 3,4-Me₂—C₆H₃ Me isoxazolin-3-yl 2931 5-Me-2- 2,4-Me₂—C₆H₃ Meisoxazolin-3-yl 2932 5-Me-2- 3-Ph—C₆H₄ Me isoxazolin-3-yl 2933 5-Me-2-4-Ph—C₆H₄ Me isoxazolin-3-yl 2934 5-Me-2- Morpholino Me isoxazolin-3-yl2935 5-Me-2- 2,6-Me₂-morpholino Me isoxazolin-3-yl 2936 5-Me-2- C₆H₅ Etisoxazolin-3-yl 2937 5-Me-2- 4-F—C₆H₄ Et isoxazolin-3-yl 2938 5-Me-2-4-Cl—C₆H₄ Et isoxazolin-3-yl 2939 5-Me-2- 4-Me—C₆H₄ Et isoxazolin-3-yl2940 5-Me-2- 3,4-Cl₂—C₆H₃ Et isoxazolin-3-yl 2941 Imidazol-1-yl C₆H₅ H¹H-NMR(CDCl₃)δppm: 4.04(3H, S), 5.18(2H, S), 7.03(1H, S), 7.15-7.17(1H,m), 7.29-7.65(9H, m), 7.90(1H, S), 8.05(1H, S) 2942 Imidazol-1-yl4-F—C₆H₄ H 2943 Imidazol-1-yl 4-Cl—C₆H₄ H mp 92.5-93.0° C. 2944Imidazol-1-yl 4-Me—C₆H₄ H 2945 Imidazol-1-yl 3,4-Cl₂—C₆H₃ H 29461-Me-imidazol-2-yl C₆H₅ H 2947 1-Me-imidazol-2-yl 4-F—C₆H₄ H 29481-Me-imidazol-2-yl 4-Cl—C₆H₄ H 2949 1-Me-imidazol-2-yl 4-Me—C₆H₄ H 29501-Me-imidazol-2-yl 3,4-Cl₂—C₆H₃ H 2951 1,2,4-Triazol-1-yl C₆H₅ H mp76.5-77.5° C. 2952 1,2,4-Triazol-1-yl 4-F—C₆H₄ H 2953 1,2,4-Triazol-1-yl4-Cl—C₆H₄ H 2954 1,2,4-Triazol-1-yl 4-Me—C₆H₄ H 2955 1,2,4-Triazol-1-yl3,4-Cl₂—C₆H₃ H 2956 5-Me-1,2,4- C₆H₅ H oxadiazol-3-yl 2957 5-Me-1,2,4-4-F—C₆H₄ H oxadiazol-3-yl 2958 5-Me-1,2,4- 4-Cl—C₆H₄ H oxadiazol-3-yl2959 5-Me-1,2,4- 4-Me—C₆H₄ H oxadiazol-3-yl 2960 5-Me-1,2,4-3,4-Cl₂—C₆H₃ H oxadiazol-3-yl 2961 Isoxazol-3-yl C₆H₅ H 2962Isoxazol-3-yl 4-F—C₆H₄ H 2963 Isoxazol-3-yl 4-Cl—C₆H₄ H 2964Isoxazol-3-yl 4-Me—C₆H₄ H 2965 Isoxazol-3-yl 3,4-Cl₂—C₆H₃ H 2966 5-Me-C₆H₅ H isoxazol-3-yl 2967 5-Me- 4-F—C₆H₄ H isoxazol-3-yl 2968 5-Me-4-Cl—C₆H₄ H isoxazol-3-yl 2969 5-Me- 4-Me—C₆H₄ H isoxazol-3-yl 29705-Me- 3,4-Cl₂—C₆H₃ H isoxazol-3-yl 2971 Isoxazol-5-yl C₆H₅ H 2972Isoxazol-5-yl 4-F—C₆H₄ H 2973 Isoxazol-5-yl 4-Cl—C₆H₄ H 2974Isoxazol-5-yl 4-Me—C₆H₄ H 2975 Isoxazol-5-yl 3,4-Cl₂—C₆H₃ H 2976 3-Me-C₆H₅ H isoxazol-5-yl 2977 3-Me- 4-F—C₆H₄ H isoxazol-5-yl 2978 3-Me-4-Cl—C₆H₄ H isoxazol-5-yl 2979 3-Me- 4-Me—C₆H₄ H isoxazol-5-yl 29803-Me- 3,4-Cl₂—C₆H₃ H isoxazol-5-yl 2981 Oxazol-5-yl C₆H₅ H mp 77-78.5°C. 2982 Oxazol-5-yl 4-F—C₆H₄ H 2983 Oxazol-5-yl 4-Cl—C₆H₄ H 2984Oxazol-5-yl 4-Me—C₆H₄ H 2985 Oxazol-5-yl 3,4-Cl₂—C₆H₃ H 29862-Isoxazolin-3-yl C₆H₅ H 2987 2-Isoxazolin-3-yl 4-F—C₆H₄ H 29882-Isoxazolin-3-yl 4-Cl—C₆H₄ H 2989 2-Isoxazolin-3-yl 4-Me—C₆H₄ H 29902-Isoxazolin-3-yl 3,4-Cl₂—C₆H₃ H 2991 Thiazolidin-2-yl C₆H₅ H 2992Thiazolidin-2-yl 4-F—C₆H₄ H 2993 Thiazolidin-2-yl 4-Cl—C₆H₄ H 2994Thiazolidin-2-yl 4-Me—C₆H₄ H 2995 Thiazolidin-2-yl 3,4-Cl₂—C₆H₃ H 29963-Me- C₆H₅ H thiazolidin-2-yl 2997 3-Me- 4-F—C₆H₄ H thiazolidin-2-yl2998 3-Me- 4-Cl—C₆H₄ H thiazolidin-2-yl 2999 3-Me- 4-Me—C₆H₄ Hthiazolidin-2-yl 3000 3-Me- 3,4-Cl₂—C₆H₃ H thiazolidin-2-yl 3001Oxazol-4-yl C₆H₅ H mp 94.5-96.0° C. 3002 Oxazol-4-yl 4-F—C₆H₄ H 3003Oxazol-4-yl 4-Cl—C₆H₄ H ¹H-NMR(CDCl₃)δppm: 2.04(3H, S), 4.14(3H, S),5.22(2H, S), 7.27-7.56(8H, m), 7.77(1H, S), 7.97(1H, S) 3004 Oxazol-4-yl4-Me—C₆H₄ H 3005 Oxazol-4-yl 3,4-Cl₂—C₆H₃ H ¹H-NMR(CDCl₃)δppm: 2.01(3H,S), 4.15(3H, S), 5.24(2H, S), 5.50-7.62(6H, m), 7.66(1H, t j=1.2),7.76(1H, S), 7.97(1H, S) 3006 Oxazol-4-yl C₆H₅ H mp 97-98° C. 3007Oxazol-4-yl 4-F—C₆H₄ H 3008 Oxazol-4-yl 4-Cl—C₆H₄ H 3009 Oxazol-4-yl4-Me—C₆H₄ H 3010 Oxazol-4-yl 3,4-Cl₂—C₆H₃ H 3011 1-Me-1H- C₆H₅ Me mp119-120° C. tetrazol-5-yl 3012 1-Me-1H- 4-F—C₆H₄ Me tetrazol-5-yl 30131-Me-1H- 4-Cl—C₆H₄ Me tetrazol-5-yl 3014 1-Me-1H- 4-Me—C₆H₄ Metetrazol-5-yl 3015 1-Me-1H- 3,4-Cl₂—C₆H₃ Me 3016 Oxazol-4-yl C₆H₅ Me¹H-NMR(CDCl₃)δppm: 2.07(3H, S), 4.15(3H, S), 5.26(2H, S), 7.35-7.77(8H,m), 7.82(1H, S), 7.97(1H, S) 3017 1-Me-1H- 4-F—C₆H₄ H tetrazol-5-yl 30181-Me-1H- 4-Cl—C₆H₄ Et tetrazol-5-yl 3019 1-Me-1H- 4-Me—C₆H₄ Ettetrazol-5-yl 3020 Oxazol-4-yl 2,4-Cl₂—C₆H₃ Me ¹H-NMR(CDCl₃)δppm:2.04(3H, s), 4.14(3H, S), 5.22(2H, S), 7.13-7.56(7H, m), 7.78(1H, S),7.98(1H, S) 3021 1,2,4-Oxadiazol-5-yl C₆H₅ Me 3022 1,2,4-Oxadiazol-5-yl4-F—C₆H₄ Me 3023 1,2,4-Oxadiazol-5-yl 4-Cl—C₆H₄ Me 30241,2,4-Oxadiazol-5-yl 4-Me—C₆H₄ Me 3025 1,2,4-Oxadiazol-5-yl 3,4-Cl₂—C₆H₃Me 3026 1,2,4-Oxadiazol-5-yl C₆H₅ H mp 120-121° C. 30271,2,4-Oxadiazol-5-yl 4-F—C₆H₄ H 3028 1,2,4-Oxadiazol-5-yl 4-Cl—C₆H₄ Et3029 1,2,4-Oxadiazol-5-yl 4-Me—C₆H₄ Et 3030 1,2,4-Oxadiazol-5-yl3,4-Cl₂—C₆H₃ Et 3031 1-Me-1,2,4- C₆H₅ Me triazol-5-yl 3032 1-Me-1,2,4-4-F—C₆H₄ Me triazol-5-yl 3033 1-Me-1,2,4- 4-Cl—C₆H₄ Me triazol-5-yl 30341-Me-1,2,4- 4-Me—C₆H₄ Me triazol-5-yl 3035 1-Me-1,2,4- 3,4-Cl₂—C₆H₃ Metriazol-5-yl 3036 1-Me-1,2,4- C₆H₅ H ¹H-NMR(CDCl₃)δppm: triazol-5-yl4.03(3H, S), 4.12(3H, S), 5.07(2H, S), 7.27-7.55(9H, m), 7.79(1H, S),7.80(1H, S) 3037 1-Me-1,2,4- 4-F—C₆H₄ H triazol-5-yl 3038 1-Me-1,2,4-4-Cl—C₆H₄ Et triazol-5-yl 3039 1-Me-1,2,4- 4-Me—C₆H₄ Et triazol-5-yl3040 1-Me-1,2,4- 3,4-Cl₂—C₆H₃ Et triazol-5-yl 3041 Imidazol-1-yl C₆H₅ Me¹H-NMR(CDCl₃)δppm: 2.09(3H, s), 4.03(3H, s), 5.28(2H, s), 7.01(1H, s),7.14(1H, d, J=2.4), 7.30- 7.62(9H, m), m), 8.03(1H, s) 3042Imidazol-1-yl 2-F—C₆H₄ Me 3043 Imidazol-1-yl 3-F—C₆H₄ Me 3044Imidazol-1-yl 4-F—C₆H₄ Me 3045 Imidazol-1-yl 2-Cl—C₆H₄ Me 3046Imidazol-1-yl 3-Cl—C₆H₄ Me 3047 Imidazol-1-yl 4-Cl—C₆H₄ Me¹H-NMR(CDCl₃)δppm: 2.07(3H, s), 4.06(3H, s), 5.18(2H, s), 7.01-7.52(10H,m), 8.01(1H, s) 3048 Imidazol-1-yl 2-Br—C₆H₄ Me 3049 Imidazol-1-yl3-Br—C₆H₄ Me 3050 Imidazol-1-yl 4-Br—C₆H₄ Me 3051 Imidazol-1-yl 3-I—C₆H₄Me 3052 Imidazol-1-yl 2-Me—C₆H₄ Me 3053 Imidazol-1-yl 3-Me—C₆H₄ Me 3054Imidazol-1-yl 4-Me—C₆H₄ Me 3055 Imidazol-1-yl 3-Et—C₆H₄ Me 3056Imidazol-1-yl 4-Et—C₆H₄ Me 3057 Imidazol-1-yl 3-MeO—C₆H₄ Me 3058Imidazol-1-yl 4-MeO—C₆H₄ Me 3059 Imidazol-1-yl 3-CF₃—C₆H₄ Me¹H-NMR(CDCl₃)δppm: 2.09(3H, s), 4.04(3H, s), 5.22(2H, s), 7.01(1H, d,J=1.2), 7.15(1H, d, J=1.2), 7.35-7.85(8H, m), 8.02(1H, s) 3060Imidazol-1-yl 4-CF₃—C₆H₄ Me 3061 Imidazol-1-yl 2,4-F₂—C₆H₃ Me 3062Imidazol-1-yl 2,5-F₂—C₆H₃ Me 3063 Imidazol-1-yl 3,4-F₂—C₆H₃ Me 3064Imidazol-1-yl 3,5-F₂—C₆H₃ Me 3065 Imidazol-1-yl 2,3-Cl₂—C₆H₃ Me 3066Imidazol-1-yl 2,4-Cl₂—C₆H₃ Me ¹H-NMR(CDCl₃)δppm: 2.06(3H, s), 4.03(3H,s), 5.16(2H, s), 7.02(1H, s), 7.13-7.52(8H, m), 8.01(1H, s) 3067Imidazol-1-yl 2,5-Cl₂—C₆H₃ Me 3068 Imidazol-1-yl 3,4-Cl₂—C₆H₃ Me¹H-NMR(CDCl₃)δppm: 2.03(3H, s), 4.04(3H, s), 5.19(2H, s), 7.01(1H, s),7.13-7.52(7H, m), 7.66(1H, s), 8.01(1H, s) 3069 Imidazol-1-yl3,5-Cl₂—C₆H₃ Me 3070 Imidazol-1-yl 3,4-Me₂—C₆H₃ Me 3071 Imidazol-1-yl2,4-Me₂—C₆H₃ Me 3072 Imidazol-1-yl 3-Ph—C₆H₄ Me 3073 Imidazol-1-yl4-Ph—C₆H₄ Me 3074 Imidazol-1-yl Morpholino Me 3075 Imidazol-1-yl2,6-Me₂-morpholino Me 3076 Imidazol-1-yl C₆H₅ Et 3077 Imidazol-1-yl4-F—C₆H₄ Et 3078 Imidazol-1-yl 4-Cl—C₆H₄ Et 3079 Imidazol-1-yl 4-Me—C₆H₄Et 3080 Imidazol-1-yl 3,4-Cl₂—C₆H₃ Et 3081 1-Me-imidazol-2-yl C₆H₅ Me3082 1-Me-imidazol-2-yl 2-F—C₆H₄ Me 3083 1-Me-imidazol-2-yl 3-F—C₆H₄ Me3084 1-Me-imidazol-2-yl 4-F—C₆H₄ Me 3085 1-Me-imidazol-2-yl 2-Cl—C₆H₄ Me3086 1-Me-imidazol-2-yl 3-Cl—C₆H₄ Me 3087 1-Me-imidazol-2-yl 4-Cl—C₆H₄Me 3088 1-Me-imidazol-2-yl 2-Br—C₆H₄ Me 3089 1-Me-imidazol-2-yl3-Br—C₆H₄ Me 3090 1-Me-imidazol-2-yl 4-Br—C₆H₄ Me 30911-Me-imidazol-2-yl 3-I—C₆H₄ Me 3092 1-Me-imidazol-2-yl 2-Me—C₆H₄ Me 30931-Me-imidazol-2-yl 3-Me—C₆H₄ Me 3094 1-Me-imidazol-2-yl 4-Me—C₆H₄ Me3095 1-Me-imidazol-2-yl 3-Et—C₆H₄ Me 3096 1-Me-imidazol-2-yl 4-Et—C₆H₄Me 3097 1-Me-imidazol-2-yl 3-MeO—C₆H₄ Me 3098 1-Me-imidazol-2-yl4-MeO—C₆H₄ Me 3099 1-Me-imidazol-2-yl 3-CF₃—C₆H₄ Me 31001-Me-imidazol-2-yl 4-CF₃—C₆H₄ Me 3101 Imidazol-1-yl Me Me¹H-NMR(CDCl₃)δppm: 1.70(3H, s), 1.78(3H, s), 4.03(3H, s), 5.01(2H, s),7.02(1H, s), 7.16(1H, d, J=1.2), 7.31-7.49(4H, m), 7.99(1H, s) 3102Imidazol-1-yl Cyclohexyl Me 3103 Imidazol-1-yl t-Bu Me 3104Imidazol-1-yl 5-Me-isoxazol-3-yl Me 3105 Imidazol-1-yl Pyridin-3-yl Me3106 1-Me-imidazol-2-yl Me Me 3107 1-Me-imidazol-2-yl Cyclohexyl Me 31081-Me-imidazol-2-yl t-Bu Me 3109 1-Me-imidazol-2-yl 5-Me-isoxazol-3-yl Me3110 1-Me-imidazol-2-yl Pyridin-3-yl Me 3111 Isoxazol-3-yl Me Me 3112Isoxazol-3-yl Cyclohexyl Me 3113 Isoxazol-3-yl t-Bu Me 3114Isoxazol-3-yl 5-Me-isoxazol-3-yl Me 3115 Isoxazol-3-yl Pyridin-3-yl Me3116 5-Me-isoxazol-3-yl Me Me 3117 5-Me-isoxazol-3-yl Cyclohexyl Me 31185-Me-isoxazol-3-yl t-Bu Me 3119 5-Me-isoxazol-3-yl 5-Me-isoxazol-3-yl Me3120 5-Me-isoxazol-3-yl Pyridin-3-yl Me 3121 3-Me-isoxazol-5-yl Me Me3122 3-Me-isoxazol-5-yl Cyclohexyl Me 3123 3-Me-isoxazol-5-yl t-Bu Me3124 3-Me-isoxazol-5-yl 5-Me-isoxazol-3-yl Me 3125 3-Me-isoxazol-5-ylPyridin-3-yl Me 3126 1,3,4-Oxadiazol-2-yl Me Me 31271,3,4-Oxadiazol-2-yl Cyclohexyl Me 3128 1,3,4-Oxadiazol-2-yl t-Bu Me3129 1,3,4-Oxadiazol-2-yl 5-Me-isoxazol-3-yl Me 31301,3,4-Oxadiazol-2-yl Pyridin-3-yl Me 3131 Thiazolidin-2-yl Me Me 3132Thiazolidin-2-yl Cyclohexyl Me 3133 Thiazolidin-2-yl t-Bu Me 3134Thiazolidin-2-yl 5-Me-isoxazol-3-yl Me 3135 Thiazolidin-2-ylPyridin-3-yl Me 3136 Pyrazol-1-yl C₆H₅ H ¹H-NMR(CDCl₃)δppm: 4.03(3H, s),4.93(2H, s), 6.43(1H, t, J=2.4), 7.31-7.60(10H, m), 7.99(1H, s),8.51(1H, d, J=2.4) 3137 Pyrazol-1-yl C₆H₅ Me 3138 Pyrazol-1-yl 4-F—C₆H₄Me 3138 Pyrazol-1-yl 4-Cl—C₆H₄ Me 3139 Pyrazol-1-yl 4-Cl—C₆H₄ Me 3140Pyrazol-1-yl 4-Me—C₆H₄ Me

The following Test Examples illustrate the effects of the fungicide ofthe present invention. (I. Controlling effects on various plant diseasesby foliage application (pot experiment))

Experimental Method

A test compound was dissolved in a small amount ofN,N-dimethylformamide, and the solution was diluted to a givenconcentration with distilled water containing a spreader. Thus, a liquidsample to be tested was prepared. The liquid sample was sprayed to testplants, and 24 hours thereafter, pathogens were inoculated by the methoddescribed below.

The percent control was calculated according to the following equation:$\text{Percent control (\%)} = {100 \times \frac{\text{severity, number of lesions,~~~~~etc. in untreated plot} - \text{severity, number of lesions,~~~~~~~~etc. in treated plot}}{\text{severity, number of lesions, etc. in untreated plot}}}$

Test Example 1 Controlling effect on Pyricularia oryzae

Two-week rice seedlings (cv.: AICHIASAHI) were transplanted in plasticcups (each 9 cm in diameter) and cultivated further 2 weeks. The testcompound in the form of a solution or a suspension was sprayed to thefoliage of the rice seedlings, to which a conidia suspension ofPyricularia oryzae cultured in an oatmeal medium was inoculated byspraying. After the inoculation, the test plant was kept in a moistchamber (28° C., 100% R.H.) for 24 hours, followed by cultivation in agreenhouse for 5 days. Six days after the inoculation, the number oflesions on the leaves of the inoculated plant was measured to calculatethe percent control.

The results are as follows.

Controlling effect on PYricularia orYzae by foliage application at 500Compound No. ppm (percent control)   1 90   5 97   6 90   7 97  13 90 15 90  16 90  39 70  40 90  61 97  81 97  105A 97  106A 97  107A 90 112A 97  113A 97  114A 90  118B 70  122A 97  131A 90  132A 70  136A 90 136B 70  141A 70  141B 70  146A 97  201 90  205 90  206 90  207 90  21570  221 70  225 70  226 70  241 70  261 70  266 90  267 90  281 70  28790  295 90  300 70  305 70  306 70  312 70  313 90  314 90  322 70  33690  436 70  512A 90  512B 97  536B 70  541B 70  605A 90  607A 90  612A90  613A 70  614B 70  636A 97  636B 70  641A 70  690A 97  705 70  706 70 712 90  713 97  716 70  722 90  731 70  732 70  741 70  801 70  812 70 912 70  936A 97 1112 97 1236 97 1310 70 1328 90 1460 90 1461 70 1554A70 1581 70 1584 70 1674 70 2799 100 2839 90 3041 90 Reference 97Fthalide

Test Example 2 Controlling effect on Sphaerotheca fuliginea

Seeds of cucumber (cv.: TSUKUBASHIROIBO) were sown in plastic cups (each9 cm in diameter), followed by cultivation for 2 to 3 weeks. The liquidtest sample in the form of a solution or suspension was sprayed on thesurface of their first leaves. The pathogen was inoculated to the leavesby spraying a conidia suspension of Sphaerotheca fuliginea which hadbeen cultured on the cucumber leaves. After the inoculation, the plantswere kept in a greenhouse at 20° C. for 10 days. Then, the infected areaon the leaf was observed, and the percent control was calculated.

The results are as follows.

Controlling effect on Sphaerotheca fuliginea by foliage application atCompound No. 500 ppm (percent control)   1 100   5 100   7 100  13 100 15 100  16 100  39 100  40 100  57 90  101A 70  104A 97  105A 100  106A100  106B 97  107A 100  112A 100  112B 90  113A 100  113B 90  114A 100 119A 97  122A 100  122B 100  130A 100  131A 100  131B 100  132A 100 136A 100  136B 100  141A 100  141B 100  144A 100  144B 70  146A 97  161100  201 100  205 100  206 100  207 100  215 100  221 97  226 70  227 97 261 97  266 97  267 100  270 97  275 100  278 97  294 97  300 70  305100  306 97  312 100  313 100  314 100  322 100  336 100  412 100  436100  512A 100  512B 100  536A 100  536B 90  541A 100  541B 100  605A 100 605B 100  606A 100  606B 100  607A 90  607B 97  612A 97  612B 100  613A100  613B 100  614B 97  636A 97  636B 100  641A 100  641B 100  690A 100 690B 100  701 100  705 97  706 100  707 100  712 100  713 100  716 100 722 100  731 100  732 100  736 100  741 100  801 100  805 97  807 100 812 100  836A 100  836B 100  844 97  905 90  912 100  936A 100  936B 971112 100 1114 70 1121 100 1122B 100 1123 90 1136 100 1161 70 1236 1001305 70 1310 90 1311 70 1312 70 1328 100 1341A 70 1341B 70 1428 100 147870 1514 97 1515 70 1581 70 1584 100 1590 70 1634A 100 1634B 70 1674 701721 100 1734 90 1735 100 1826 70 2001 70 2012 100 2014 100 2036 1002044 97 2120 70 2507 100 2528 100 2799 100 2839 100 3041 97 Reference 97Fenarimol

Test Example 3 Controlling effect on Botrytis cinerea

The seeds of cucumber (cv.: TSUKUBASHIROIBO) were sown in plastic cups(each 9 cm in diameter), followed by cultivation for 2 to 3 weeks. Thetest compound in the form of a solution or suspension was sprayed to thesurface of their first leaves, and mycelial disks (4 mm φ) of Botrytiscinerea cultured on the potato sucrose agar medium were put on the leafsurfaces to inoculate. the cucumber seedlings with the pathogen. Theplants were kept in a moist chamber at 20° C. for 3 days. The diameterof the lesions on the leaves was measured and the percent control wascalculated.

The results are as follows.

Controlling effect on Botrytis cinerea by foliage application at 500 ppmCompound No. (percent control)  1 100  5 70  6 100  7 100  13 70  15 100 40 70  61 100  81 90 106A 70 122A 70 130A 70 132A 70 141A 90 144A 70201 70 205 70 206 97 207 100 215 97 314 70 605A 70 607A 70 713 70 732 70741 90 Reference 97 Fenarimol

Test Example 4 Controlling effect on Erysiphe graminis f. sp. tritici.

The seeds of wheat (cv.: NORIN No. 61) were sown in plastic cups (each 9cm in diameter), followed by cultivation for 2 to 3 weeks. The testcompound in the form of a solution or suspension was sprayed to theseedlings, and conidia of Erysiphe graminis f. sp. tritici cultured onwheat leaves were dropped on the test plants to inoculate the plantswith the pathogen. After the inoculation, the plants were kept in agreenhouse at 20° C. for 10 days. The infected area on the leaf wasobserved, and the percent control was calculated.

The results are as follows.

Controlling effect on ErYsiphe graminis f. sp. tritici by foliageapplication at 500 ppm Compound No. (percent control)   1 90   5 90   6100   7 100  13 90  15 97  16 90  40 97  57 70  61 97  81 97  104A 90 104B 70  105A 70  106A 70  107A 70  112A 100  113A 90  114A 90  122A 97 131A 90  132A 70  136A 90  136B 70  141A 90  161 70  201 90  206 90 207 100  215 90  221 70  226 70  227 70  235 90  261 97  265 70  266 97 267 97  270 90  275 90  278 90  281 90  295 90  305 90  306 70  312 100 313 70  314 70  322 70  336 97  412 70  436 90  512A 97  512B 97  536A97  536B 100  541A 90  541B 90  605A 90  605B 90  606A 70  607A 90  607B70  612A 100  612B 100  613A 90  613B 70  614B 70  636A 100  636B 100 641A 90  641B 90  690A 100  690B 100  701 70  706 90  707 90  712 100 713 90  716 70  722 90  731 70  732 70  736 100  741 90  801 90  812100  36A 97  836B 97  912 90  936A 97  936B 90 1101 90 1112 90 1114 701121 90 1122A 70 1122B 90 1123 90 1136 90 1161 90 1236 90 1310 90 131170 1328 90 1341A 90 1341B 90 1428 70 1455 70 1460 90 1478 90 1514 701515 90 1554A 70 1554B 70 1584 100 1634A 97 1654 70 1665 70 1667 70 167470 1721 90 1734 70 1735 97 1829 90 2012 70 2036 90 2799 97 2839 97Reference 97 Fenarimol

Test Example 5 Controlling effect on Puccinia coronata

The seeds of oat (cv.: PC-38) were sown in plastic cups (each 9 cm indiameter), followed by cultivation for 2 to 3 weeks. The test compoundin the form of a solution or suspension was sprayed to the seedlings.Spores of Puccinia coronata cultured on oat leaves were collected,diluted about 10-fold with talc, and sprayed to the test plants toinoculate the plants with the pathogen. After the inoculation, theplants were kept in a moist chamber at 20° C. for 1 day and then in agreenhouse at 20° C. for 8 days. The infected area on the leaf wasobserved, and the percent control was calculated.

The results are as follows.

Controllng effect on Puccinia coronata by foliage application CompoundNo. at 500 ppm (percent control)   1 97   5 90   6 100   7 97  13 97  15100  16 100  40 70  57 90  61 97  81 97  112A 100  136A 100  136B 97 161 97  201 90  205 70  206 97  207 97  215 90  267 90  275 90  278 90 298 70  312 97  336 100  436 90  536A 90  536B 97  612A 97  636A 100 636B 90  701 97  712 100  722 97  736 100  801 97  914 97  936A 90 100170 1112 70 1113 70 1136 90 1236 97 1328 70 1478 70 1584 70 1721 70 200170 Reference 97 Fenarimol

Test Example 6 Controlling effect on Pseudoperonospora cubensis

The seeds of cucumber (var.: TSUKUBASHIROIBO) were sown in plastic cups(each 9 cm in diameter), followed by cultivation for 2 to 3 weeks. Thetest compound in the form of a solution or suspension was sprayed to thesurface of their first leaves, and a zoosporangia suspension ofPseudoperonospora cubensis cultured on cucumber leaves was dropped onthe above leaf surfaces to inoculate the test plants with the pathogen.After the inoculation, the plants were kept in a moist chamber at 20° C.for 10 days. Then, the area of the lesions around the inoculum wereobserved and the percent control was calculated.

The results are as follows.

Controlling effect on Pseudoperonospora cubensis by foliage applicationat 500 ppm Compound No. (percent control)  105A 100  106A 100  106B 100 112A 97  113A 100  119A 85  122A 100  130A 100  131A 100  132A 100 141A 100  144A 100  146A 100  305 100  306 100  313 100  314 100  412100  512A 100  512B 100  536B 100  541A 100  541B 100  605A 100  606A 95 606B 100  607A 97  607B 97  612A 100  612B 100  613A 70  613B 100  614B100  641A 100  690A 100  690B 100  701 100  705 100  706 100  713 100 716 100  722 100  731 100  732 100  741 100  801 100  844 100  905 991721 100 2014 100 2044 100 2507 100 2528 100 2799 95 2839 95 Reference97 Benalaxyl

As described above, the present invention provides a novel oximederivative, particularly a heterocyclic compound substituted withα-(O-substituted oxyimino)-2-substituted benzyl, having potentfungicidal activity, a process for producing it, intermediates therefor,and a fungicide containing it as an active ingredient.

What is claimed is:
 1. A compound of the formula (I):

wherein R¹ is a group of the formula (a):

wherein R⁹ and R¹⁰ are the same or different and are hydrogen,optionally substituted alkyl, acyl, alkylthio, alkylsulfinylalkylsulfonyl, optionally substituted amino, cycloalkyl, optionallysubstituted aryl or an optionally substituted heterocyclic group, or R⁹and R¹⁰ are linked together to form a monocyclic or polycyclic ringwhich may contain a heteroatom, R² is alkyl, alkenyl, alkynyl orcycloalkyl; R³ is an optionally substituted imidazolyl or imidazolinyl;R⁴ is a hydrogen, alkyl, alkoxy, halogen, nitro, cyano or halogenatedalkyl; M is an oxygen atom, S(O)i (in which i is 0, 1 or 2), NR¹⁶ (inwhich R¹⁶ is hydrogen, alkyl or acyl) or a single bond; n is 0 or 1,provided that when R³ is imidazolyl, n is 1; and indicates an E- orZ-isomer of a mixture thereof; or a salt thereof.
 2. A compoundaccording to claim 1, wherein R⁹ and R¹⁰ are the same or different andare hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, optionallysubstituted phenyl, optionally substituted naphthyl or an optionallysubstituted heterocyclic group, or R⁹ and R¹⁰ are linked together toform a cyclopentane or cyclohexane ring which may form a condensed ringwith another ring, or a salt thereof.
 3. A compound according to claim1, wherein R⁹ is phenyl which is unsubstituted or substituted with 1 to3 substituents selected from the group consisting of halogen, optionallysubstituted alkyl, optionally substituted hydroxyl, alkylthio,optionally substituted amino, nitro, phenyl and cyano, or a saltthereof.
 4. A compound according to claim 1, wherein R⁹ is phenyl whichis unsubstituted or substituted with 1 to 3 substituents selected fromthe group consisting of chlorine, methyl, trifluoromethyl and methoxy,or a salt thereof.
 5. A compound according to claim 1, wherein R⁹ ismorpholino, pyridyl, pyridazinyl, pyrazolyl, pyrimidinyl, furyl,thienyl, oxazolyl, isoxazolyl, benzothiazolyl, quinolyl, quinazoliriylor pyrazinyl, each of which is unsubstituted or substituted, or a saltthereof.
 6. A compound according to claim 1, wherein R¹⁰ is hydrogen oralkyl, or a salt thereof.
 7. A compound according to claim 1, whereinR¹⁰ is hydrogen, methyl or ethyl, or a salt thereof.
 8. A compoundaccording to claim 1, wherein R³ is imidazolyl; imidazolyl substitutedwith lower alkyl; imidazolinyl; or imidazolinyl substituted with loweralkyl; or a salt thereof.
 9. A compound according to claim 1, wherein Mis an oxygen atom, or a salt thereof.
 10. A compound of formula (V):

R¹ is a group of the formula (a):

wherein R⁹ and R¹⁰ are the same or different and are hydrogen,optionally substituted alkyl, acyl, alkylthio, alkylsulfinylalkylsulfonyl, optionally substituted amino, cycloalkyl, optionallysubstituted aryl or an optionally substituted heterocyclic group, or R⁹and R¹⁰ are linked together to form a monocyclic or polycyclic ringwhich may contain a heteroatom, R² is alkyl, alkenyl, alkynyl orcycloalkyl; R³ is an optionally substituted imidazolyl or imidazolinyl;R⁴ is a hydrogen, alkyl, alkoxy, halogen, nitro, cyano or halogenatedalkyl; and M is an oxygen atom, or a salt thereof.
 11. A compound of theformula (XIV):

wherein each symbol is as defined in claim 1 or a salt thereof.
 12. Acompound according to claim 11, wherein M is an oxygen atom, or a saltthereof.